Name: 622-30-0|N-Benzylhydroxylamine|95%
Brand: Ambeed
SKU: A155394
Rating: 90 (35 reviews)

1
[ 100-44-7 ]
[ 622-30-0 ]
[ 621-07-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1890,vol. 257,p. 225
[2]Asian Journal of Chemistry,2017,vol. 29,p. 885 - 887

2
[ 100-44-7 ]
[ 621-07-8 ]
[ 620-40-6 ]
[ 622-30-0 ]
[ 100-46-9 ]
[ 103-49-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1890,vol. 257,p. 225

3
[ 64-17-5 ]
[ 622-30-0 ]
[ 6780-49-0 ]
N-benzyl-N-hydroxy-N'-phenyl-formamidine [ No CAS ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 704

4
[ 622-30-0 ]
[ 6780-49-0 ]
N-benzyl-N-hydroxy-N'-phenyl-formamidine [ No CAS ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 704

5
[ 932-90-1 ]
[ 622-30-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With K₁₂(Ga₄(1,5-bis(2,3-dihydroxybenzamido)naphthalene))6; potassium phosphate; borane pyridine In water-d2 at 20℃; for 22h; Inert atmosphere; Sealed tube;
95%	With Benzyltriethylammonium borohydride for 0.133333h; solid-phase conditions;
80%	With sodium cyanoborohydride at 20℃;

74%	With butyl triphenylphosphonium tetraborate at 20℃; for 0.233333h;
58%	With 1-benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate In <i>tert</i>-butyl alcohol at 20℃; for 1.2h;
48%	With boron trifluoride diethyl etherate; tri-n-butyl-tin hydride In dichloromethane at 20℃; for 2h;
43%	With hydrogenchloride; methanol; sodium cyanoborohydride
	With pyridine; hydrogenchloride; diborane In ethanol
	With hydrogenchloride; sodium cyanoborohydride In methanol
	With sodium cyanoborohydride In methanol
	With diborane In tetrahydrofuran for 4h; Ambient temperature;
70 % Spectr.	With Benzeneselenol Irradiation;
	With hydrogenchloride; sodium cyanoborohydride In methanol at 20℃; for 2h;
	With sodium cyanoborohydride; acetyl chloride In methanol at 20℃; for 3h;
	With hydrogenchloride; sodium cyanoborohydride In methanol; water at 20℃;
	Inert atmosphere;
	With hydrogenchloride; sodium cyanoborohydride In methanol
	With hydrogenchloride; sodium cyanoborohydride In methanol; water
	With hydrogenchloride; sodium cyanoborohydride In methanol; water at 20℃; for 4h; Inert atmosphere;
	With hydrogenchloride; sodium cyanoborohydride In methanol; water at 0 - 20℃; for 4h;	12.2 2 Synthesis of intermediate 30 Compound 30b (2.28 g, 18.87 mmol) was dissolved in 30 mL of methanol.Sodium cyanoborohydride (2.02 g, 32.08 mmol) was added with stirring at 0 ° C, then 12N concentrated hydrochloric acid was slowly added dropwise and reacted at room temperature for 4 h.After the reaction of the starting material was completed, the pH was adjusted to 9 with a 6N aqueous sodium hydroxide solution, and then extracted with dichloromethane.After drying and concentration, 1.69 g of crude material was obtained as a white solid, yield 73%.
	With hydrogenchloride; sodium cyanoborohydride In methanol; water at 20℃;

Reference： [1]Morimoto, Mariko; Cao, Wendy; Bergman, Robert G.; Raymond, Kenneth N.; Toste, F. Dean [Journal of the American Chemical Society, 2021, vol. 143, # 4, p. 2108 - 2114]
[2]Gopalakrishnan, Mannathusamy; Anandabaskaran, Thirunavukkarasu; Sureshkumar, Purusothaman; Thanusu, Jayaraman; Kumaran, Arumugam K.; Kanagarajan, Vijayakumar [Mendeleev Communications, 2006, vol. 16, # 1, p. 50 - 51]
[3]Zhang, Chen; Liu, Hongrui; Yang, Qing; Chang, Jun; Sun, Xun [Chinese Journal of Chemistry, 2013, vol. 31, # 1, p. 154 - 158]
[4]Hajipour; Mohammadpoor-Baltork; Noroallhi [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 2, p. 152 - 156]
[5]Hajipour; Mohammadpoor-Baltork; Rahi [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 3, p. 239 - 242]
[6]Ueda, Masafumi; Miyabe, Hideto; Namba, Megumi; Nakabayashi, Toshiki; Naito, Takeaki [Tetrahedron Letters, 2002, vol. 43, # 24, p. 4369 - 4371]
[7]Meadows, Margaret K.; Roesner, Emily K.; Lynch, Vincent M.; James, Tony D.; Anslyn, Eric V. [Organic Letters, 2017, vol. 19, # 12, p. 3179 - 3182]
[8]Kawase,M.; Kikugawa,Y. [Journal of the Chemical Society. Perkin transactions I, 1979, p. 643 - 645]
[9]Borch,R.F. et al. [Journal of the American Chemical Society, 1971, vol. 93, p. 2897 - 2904]
[10]Fray, M. Jonathan; Jones, Richard H.; Thomas, Eric J. [Journal of the Chemical Society. Perkin transactions I, 1985, p. 2753 - 2762]
[11]Elfarra; Yeh; Hanna [Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1189 - 1192]
[12]Perkins, M. John; Smith, Brian V.; Turner, Eric S. [Journal of the Chemical Society. Chemical communications, 1980, # 20, p. 977 - 978]
[13]Fang, Lei; Chan, Wing-Hong; He, Yong-Bing [Tetrahedron Letters, 2005, vol. 46, # 1, p. 173 - 176]
[14]Evans, David A.; Song, Hyun-Ji; Fandrick, Keith R. [Organic Letters, 2006, vol. 8, # 15, p. 3351 - 3354]
[15]Location in patent: experimental part Wu, Kaicheng; Chen, Yali; Lin, Yibei; Cao, Weiguo; Zhang, Min; Chen, Jie; Lee, Albert W.M. [Tetrahedron, 2010, vol. 66, # 3, p. 578 - 582]
[16]MacDonald, Melissa J.; Hesp, Colin R.; Schipper, Derek J.; Pesant, Marc; Beauchemin, André M. [Chemistry - A European Journal, 2013, vol. 19, # 8, p. 2597 - 2601]
[17]Li, Pan; Wu, Chunrui; Zhao, Jingjing; Li, Yang; Xue, Weichao; Shi, Feng [Canadian Journal of Chemistry, 2013, vol. 91, # 1, p. 43 - 50]
[18]Biswas, Suvendu; Abo-Dya, Nader E.; Oliferenko, Alexander; Khiabani, Amir; Steel, Peter J.; Alamry, Khalid A.; Katritzky, Alan R. [Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8502 - 8509]
[19]Pagoti, Sreenivasarao; Dutta, Debasish; Dash, Jyotirmayee [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3532 - 3538]
[20]Current Patent Assignee: XIHUA UNIVERSITY - CN108689937, 2018, A Location in patent: Paragraph 0210; 0212; 0215; 0216
[21]He, Chun-Ting; Han, Xiao-Li; Zhang, Yan-Xue; Du, Zhen-Ting; Si, Chang-Mei; Wei, Bang-Guo [Organic and Biomolecular Chemistry, 2021, vol. 19, # 2, p. 457 - 466]

6
syn-benzaldehyde oxime [ No CAS ]
[ 622-30-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium cyanoborohydride; acetyl chloride In methanol at 0℃;
87%	With hydrogenchloride; sodium cyanoborohydride In methanol at 25℃; for 4h;
61%	With hydrogenchloride; sodium cyanoborohydride In methanol

49%

With hydrogenchloride; sodium cyanoborohydride In methanol at 20℃; for 3h;

4.4 Step 4: Synthesis of N-benzylhydrox lamine To a solution of (E)-benzaldehyde oxime (16 g, 130 mmol) and sodium cyanoborohydride (15 g, 190 mmol) in methanol (200ml) at 0 °C was added cone. HC1 (20 mL, 260 mmol) drop wise. After the addition was complete the reaction mixture stirred at room temperature for 3 hrs. The reaction mixture was brought to pH 9 with 6N NaOH and concentrated under vacuum to remove MeOH. The desired product was extracted in DCM and the organic layer was washed with brine, dried over sodium sulfate and concentrated to give an oil. The material was triturated using ethyl acetate and hexanes to afford N-benzylhydroxylamine as a white solid. (8 g, 49%) 1H NMR (400 MHz, DMSO-de): δ 7.35-7.20 (m, 5H), 5.99 (s, 1H), 3.861 (s, 2H). LCMS: m/z = 124.0 [M+H]+.

Reference： [1]Maskill, H.; Jencks, William P. [Journal of the American Chemical Society, 1987, vol. 109, # 7, p. 2062 - 2070]
[2]Aschwanden, Patrick; Kvaerno, Lisbet; Geisser, Roger W.; Kleinbeck, Florian; Carreira, Erick M. [Organic Letters, 2005, vol. 7, # 25, p. 5741 - 5742]
[3]Yang, Rong-Hua; Chan, Wing-Hong; Lee, Albert W. M.; Xia, Ping-Fang; Zhang, Hong-Kui; Li, Ke'An [Journal of the American Chemical Society, 2003, vol. 125, # 10, p. 2884 - 2885]
[4]Current Patent Assignee: EPIZYME, INC. - WO2016/40504, 2016, A1 Location in patent: Paragraph 0202

7
[ 100-39-0 ]
[ 622-33-3 ]
[ 622-30-0 ]
[ 621-07-8 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 2955 - 2956

8
[ 100-52-7 ]
[ 622-30-0 ]
[ 3376-26-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With magnesium sulfate In dichloromethane for 15h;
85%	With sodium sulfate In dichloromethane Ambient temperature;
73%	With sodium sulfate In dichloromethane at 20℃;

62%	With magnesium sulfate In dichloromethane for 4h; Ambient temperature;
	With sodium acetate In ethanol Ambient temperature; Yield given;
	Micellar solution;
	With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;
	In ethanol at 20℃; Darkness;
	With micelle
	In ethanol at 20℃;
	Inert atmosphere;

Reference： [1]Aschwanden, Patrick; Kvaerno, Lisbet; Geisser, Roger W.; Kleinbeck, Florian; Carreira, Erick M. [Organic Letters, 2005, vol. 7, # 25, p. 5741 - 5742]
[2]Yakura; Nakazawa; Takino; Ikeda [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 8, p. 2014 - 2018]
[3]Hay, Michael B.; Wolfe, John P. [Angewandte Chemie - International Edition, 2007, vol. 46, # 34, p. 6492 - 6494]
[4]Dondoni; Franco; Junquera; Merchan; Merino; Tejero [Synthetic Communications, 1994, vol. 24, # 18, p. 2537 - 2550]
[5]Sain, Bir; Prajapati, Dipak; Mahajan, Asha R; Sandhu, Jagir S [Bulletin de la Societe Chimique de France, 1994, vol. 131, # 3, p. 313 - 316]
[6]Location in patent: body text McKay, Craig S.; Moran, Joseph; Pezacki, John Paul [Chemical Communications, 2010, vol. 46, # 6, p. 931 - 933]
[7]Location in patent: experimental part Wu, Kaicheng; Chen, Yali; Lin, Yibei; Cao, Weiguo; Zhang, Min; Chen, Jie; Lee, Albert W.M. [Tetrahedron, 2010, vol. 66, # 3, p. 578 - 582]
[8]Barroso, Santiago; Blay, Gonzalo; Munoz, M. Carmen; Pedro, Jose R. [Organic Letters, 2011, vol. 13, # 3, p. 402 - 405]
[9]Mackenzie, Douglas A.; Pezacki, John Paul [Canadian Journal of Chemistry, 2014, vol. 92, # 4, p. 337 - 340]
[10]Xie, Lei; Yu, Xuan; Li, Jiaqi; Zhang, Zhenhua; Qin, Zhaohai; Fu, Bin [European Journal of Organic Chemistry, 2017, vol. 2017, # 3, p. 657 - 661]
[11]Zhang, Ming; Kumagai, Naoya; Shibasaki, Masakatsu [Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12450 - 12455]

9
[ 75-07-0 ]
[ 622-30-0 ]
[ 243140-08-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane at 20℃; for 1h;	7 Example 7. Synthesis of compound 5 (Z)-N-Ethylidene-l-phenylmethanamine N -oxide (ba)The synthesis of this compound was described in the literature. See: J.-N. Denis, H.Mauger, Y. Vallee Tetrahedron Lett. 1997, 38, 8515-8518; H. Chalaye-Mauger, J.-N. Denis, M.- T. Averbuch-Pouchot, Y. Vallee Tetrahedron 2000, 56, 791-804. It was prepared according to the procedure described in these references.In a dry flask, freshly distilled acetaldehyde (1.39 g, 31.5 mmol) was dissolved in dry dichloromethane (50 mL). To this solution, N-benzylhydroxylamine (3.70 g, 30 mmol) and excess of anhydrous MgSC>4 (15 g) were added. The mixture was stirred for 1 hour at room temperature under argon. The solution was then filtered through a short pad of celite to remove MgSC>4 and concentrated under vacuum. The desired product (ba) was obtained without any further purification as a white solid. Yield: 100%.1H NMR (300 MHz, DMSO-d6): δ = 1.82 (d, J = 5.7 Hz, 3H, CH3), 4.87 (s, 2H, CH2), 7.21 (q, J = 5.7 Hz, 1H, CH), 7.29-7.43 (m, 5H, CH) ppm. 13C NMR (75.5 MHz, DMSO-d6): δ = 12.2 (CH3), 67.7 (CH2), 127.8 (CH), 128.2 (CH), 128.8 (CH), 133.0 (CH), 134.5 (C) ppm. LRMS (ESI): m/z = 150 [(M+H)+].
55%	With sodium sulfate In dichloromethane Ambient temperature;

Reference： [1]Current Patent Assignee: COMMUNITY GRENOBLE ALPES UNIVERSITY - WO2013/14104, 2013, A1 Location in patent: Page/Page column 42
[2]Yakura; Nakazawa; Takino; Ikeda [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 8, p. 2014 - 2018]

10
[ 75-07-0 ]
[ 622-30-0 ]
[ 139189-66-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;	4.1.1 (Z)-N-ethylidene-1-phenylmethanamine N-oxide (ba) In a dry flask, freshly distilled acetaldehyde (1.39 g, 31.5 mmol) was dissolved in dry dichloromethane (50 mL). To this solution, N-hydroxybenzylamine (3.70 g, 30 mmol) and anhydrous MgSO4 (15 g) were added. The mixture was stirred for 1 hour at room temperature under argon. The solution was then filtered through a short pad of celite to remove MgSO4 and concentrated under vacuum. The desired product (ba) was obtained without any further purification as a white solid. Yield: 100%. 1H NMR (300 MHz, DMSO-d6): δ = 1.82 (d, J = 5.7 Hz, 3H, CH3), 4.87 (s, 2H, CH2), 7.21 (q, J = 5.7 Hz, 1H, CH), 7.29-7.43 (m, 5H, CH) ppm. 13C NMR (75.5 MHz, DMSO-d6): δ = 12.2 (CH3), 67.7 (CH2), 127.8 (CH), 128.2 (CH), 128.8 (CH), 133.0 (CH), 134.5 (C) ppm. LRMS (ESI): m/z = 150 [(M+H)+].
100%	With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;	7 Example 7. Synthesis of compound 5 (Z)-N-Ethylidene-1-phenylmethanamine N-oxide (ba) In a dry flask, freshly distilled acetaldehyde (1.39 g, 31.5 mmol) was dissolved in dry dichloromethane (50 mL). To this solution, N-benzylhydroxylamine (3.70 g, 30 mmol) and excess of anhydrous MgSO4 (15 g) were added. The mixture was stirred for 1 hour at room temperature under argon. The solution was then filtered through a short pad of celite to remove MgSO4 and concentrated under vacuum. The desired product (ba) was obtained without any further purification as a white solid. Yield: 100%. 1H NMR (300 MHz, DMSO-d6): δ = 1.82 (d, J = 5.7 Hz, 3H, CH3), 4.87 (s, 2H, CH2), 7.21 (q, J = 5.7 Hz, 1H, CH), 7.29-7.43 (m, 5H, CH) ppm. 13C NMR (75.5 MHz, DMSO-d6): δ = 12.2 (CH3), 67.7 (CH2), 127.8 (CH), 128.2 (CH), 128.8 (CH), 133.0 (CH), 134.5 (C) ppm. LRMS (ESI): m/z = 150 [(M+H)+].
100%	With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;	4.1.1 Synthesis of compound (gb) (Z)-N-Ethylidene-l-phenylmethanamine N -oxide (ba) In a dry flask, freshly distilled acetaldehyde (1.39 g, 31.5 mmol) was dissolved in dry dichloromethane (50 mL). To this solution, N-hydroxybenzylamine (3.70 g, 30 mmol) and anhydrous MgS04 (15 g) were added. The mixture was stirred for 1 hour at room temperature under argon. The solution was then filtered through a short pad of celite to remove MgS04 and concentrated under vacuum. The desired product (ba) was obtained without any further purification as a white solid. Yield: 100%.1H NMR (300 MHz, DMSO-d6): δ = 1.82 (d, J = 5.7 Hz, 3H, CH3), 4.87 (s, 2H, CH2), 7.21 (q, J = 5.7 Hz, 1H, CH), 7.29-7.43 (m, 5H, CH) ppm. 13C NMR (75.5 MHz, DMSO-d6): δ = 12.2 (CH3), 67.7 (CH2), 127.8 (CH), 128.2 (CH), 128.8 (CH), 133.0 (CH), 134.5 (C) ppm. LRMS (ESI): m/z = 150 [(M+H)+].

92%	With sodium hydrogencarbonate; sodium sulfate In dichloromethane at 0℃; for 1h;
	In dichloromethane Ambient temperature;
	With potassium carbonate In dichloromethane; water at 20℃; for 30h;

Reference： [1]Current Patent Assignee: COMMUNITY GRENOBLE ALPES UNIVERSITY - EP2548864, 2013, A1 Location in patent: Paragraph 0294; 0295
[2]Current Patent Assignee: COMMUNITY GRENOBLE ALPES UNIVERSITY - EP2548865, 2013, A1 Location in patent: Paragraph 0232-0233
[3]Current Patent Assignee: COMMUNITY GRENOBLE ALPES UNIVERSITY - WO2013/14102, 2013, A1 Location in patent: Page/Page column 59
[4]Aschwanden, Patrick; Kvaerno, Lisbet; Geisser, Roger W.; Kleinbeck, Florian; Carreira, Erick M. [Organic Letters, 2005, vol. 7, # 25, p. 5741 - 5742]
[5]Panfil; Belzecki; Urbanczyk-Lipkowska; Chmielewski [Tetrahedron, 1991, vol. 47, # 48, p. 10087 - 10094]
[6]Kawakami; Ohtake; Arakawa; Okachi; Imada; Murahashi [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 11, p. 2423 - 2444]

11
[ 50-00-0 ]
[ 75266-40-9 ]
[ 622-30-0 ]
[ 107942-07-4 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 2179 - 2183

12
[ 111969-64-3 ]
[ 622-30-0 ]
[ 85252-42-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1593 - 1598

13
[ 622-30-0 ]
[ 653-35-0 ]
N-benzyl-N-2,3,4,5,6-pentafluorobenzylhydroxylamine [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1987,vol. 36,p. 247 - 272

14
[ 622-30-0 ]
[ 4547-02-8 ]
[ 77176-00-2 ]

Reference： [1]Archiv der Pharmazie,1980,vol. 313,p. 926 - 936

15
[ 622-30-0 ]
[ 942-91-6 ]
[ 95096-10-9 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5198 - 5209

16
[ 622-30-0 ]
[ 28571-11-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride; sodium nitrite In methanol; water at 0℃; for 0.0833333h;
	Multi-step reaction with 2 steps 1: gaseous HCl / diethyl ether / 15 °C 2: 76 percent / NaNO₂ / H₂O / 0.5 h / 0 - 3 °C

Reference： [1]Maskill, H.; Jencks, William P. [Journal of the American Chemical Society, 1987, vol. 109, # 7, p. 2062 - 2070]
[2]Nakajima, Masayuki; Anselme, Jean-Pierre [Journal of Organic Chemistry, 1983, vol. 48, # 9, p. 1444 - 1448]

17
[ 622-30-0 ]
[ 15186-48-8 ]
[ 1165677-00-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium sulfate In dichloromethane at 20℃; for 16.5h; Inert atmosphere;	19.4 (S,Z)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 1.50 g (11.53 mmol) (R)-2,2-Dimethyl-1.3-dioxolane-4-carboxaldehyde (Fluorochem, Hadfield, UK) was dissolved in 60 ml of DCM and treated with 1.64 g (11.53 mmol) sodium sulfate. The reaction mixture was flushed with argon and treated with a solution of 1.42 g (11.53 mmol) N-benzyl-hydroxylamine (prepared from the commercially available hydrochloride salt) in 20 ml of CH2Cl2. The reaction mixture was stirred under argon at RT for 16.5 h and then filtered. Silicagel was added to the filtrate is and preabsorbed, before being purified by chromatography on silicagel (gradient: Heptane/EtOAc 0%-100% in 30 min). Fr. 20-80 were collected and evaporated to dryness and dried under vacuum overnight to give 1.48 g of a white solid (˜100% pure by HPLC, Rt=1.43); ESI-MS: 236.2 [M+H]+(LC-MS 1))
95%	With magnesium sulfate In dichloromethane for 2h;
94%	With magnesium sulfate In dichloromethane at 20℃;

86%	With magnesium sulfate In dichloromethane for 4h; Ambient temperature;
85%	With sodium sulfate In dichloromethane for 15h; Ambient temperature;
83%	With sodium sulfate In dichloromethane for 10h; Ambient temperature;
82%	With magnesium sulfate In dichloromethane at 20℃; for 4h;
57%	With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2013/225574, 2013, A1 Location in patent: Paragraph 0637; 0638
[2]Masson, Géraldine; Zeghida, Walid; Cividino, Pascale; Py, Sandrine; Vallée, Yannick [Synlett, 2003, # 10, p. 1527 - 1529]
[3]Degiorgis, Fabio; Lombardo, Marco; Trombini, Claudio [Tetrahedron, 1997, vol. 53, # 34, p. 11721 - 11730]
[4]Dondoni; Franco; Junquera; Merchan; Merino; Tejero [Synthetic Communications, 1994, vol. 24, # 18, p. 2537 - 2550]
[5]Kita, Yasuyuki; Tamura, Osamu; Itoh, Fumio; Kishino, Hiroko; Miki, Takashi; et al. [Chemical and pharmaceutical bulletin, 1989, vol. 37, # 8, p. 2002 - 2007]
[6]Dondoni; Junquera; Merchan; Merino; Tejero [Tetrahedron Letters, 1992, vol. 33, # 29, p. 4221 - 4224]
[7]Merino, Pedro; Franco, Santiago; Merchan, Francisco L.; Tejero, Tomas [Tetrahedron Asymmetry, 1997, vol. 8, # 20, p. 3489 - 3496]
[8]Xiao, Zu-Feng; Ding, Ting-Hui; Mao, Sheng-Wei; Ning, Xiao-Shan; Kang, Yan-Biao [Advanced Synthesis and Catalysis, 2016, vol. 358, # 11, p. 1859 - 1863]

18
[ 160549-10-0 ]
[ 622-30-0 ]
[ 260789-53-5 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 9375 - 9378
[2]Journal of Organic Chemistry,2002,vol. 67,p. 7203 - 7214

19
[ 64-17-5 ]
[ 100-44-7 ]
[ 622-30-0 ]
natrium carbonate [ No CAS ]
[ 621-07-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1890,vol. 257,p. 225

20
[ 1885-38-7 ]
[ 622-30-0 ]
N-benzyl-α-((cyanomethyl)benzyl)hydroxylamine [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 8251 - 8254

21
[ 32042-38-9 ]
[ 622-30-0 ]
[ 31335-70-3 ]

Reference： [1]Organic letters,2002,vol. 4,p. 111 - 113

22
[ 622-30-0 ]
[ 613672-39-2 ]
[ 613672-40-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With magnesium bis(trifluoromethane solfonyl)imide In dichloromethane at -40℃; Inert atmosphere;	1.16 Our experiments began with addition of N-benzyl hydroxylamine to tiglates (8-17) with different achiral templates using catalytic amounts (5-30 mol %) of a chiral Lewis acid derived from ligand 18 and magnesium salts, as shown in Table 1. That the same isoxazolidinone product formed regardless of template streamlined our assessment of enantioselectivity. Results from these studies are also shown in Table 1. TABLE 1 EntrySMa R3 R4 Lewis Acid T ° C.Yieldb dec eed 1 8-CH2CH2CH2-Mg(ClO4)2 -40 10 95 70 2 9-CH2CH2O-Mg(ClO4)2 -40 8 95 40 3 10 Me PhMg(ClO4)2 -40 10 60 18 4 11 H PhMg(ClO4)2 -40 47 94 75 5 11 H PhMg(ClO4)2 25 66 90 45 6 12 H3,5-(CF3)2-PhMg(ClO4)2 25 70 92 40 7 13 H3,5-(NO2)2-PhMg(ClO4)2 25 66 90 44 8 14 H4-NO2-PhMg(ClO4)2 25 62 94 46 9 15 H t-butylMg(ClO4)2 25 45 92 57 10 16 H cyclohexylMg(ClO4)2 25 64 88 67 11 16 H cyclohexylMg(ClO4)2 -40 76 92 88 12 16 H cyclohexylMg(Ntf2)2 -40 66 90 96 13 16 H cyclohexylMgI2 -40 62 90 70 14 17 H i-propylMg(ClO4)2 25 78 94 54 15 17 H i-propylMg(ClO4)2 -40 76 96 90 16 17 H i-propylMg(Ntf2)2 -40 72 96 96 aSM = starting materialbisolated yield after column chromatographycdiastereomeric excess determined by 1H-NMR (500 MHz)ddetermined by chiral HPLCConjugate amine addition to pyrrolidinone (8) or oxazolidinone (9) derived tiglate gave low yields, although the diastereoselectivity and enantioselectivity were good (entries 1 and 2 in Table 1). With regard to diastereoselectivity, the major diastereomer of 18 had trans stereochemistry for the substituents as established by NMR. This is believed to be a consequence of the syn addition of the amine to the substrate in a concerted manner. Reaction with tertiary imide 10 (R3=CH3) was also very slow and low-yielding, and this reaction gave 19 with low selectivity (entry 3 in Table 1). By contrast, secondary imides 11-17 (R3=H), lacking the A1,3 strain present in 8-10, were much more reactive and gave good yields. Our initial attempt with benzimide 11 (entry 4 in Table 1) gave excellent diastereoselectivity and good enantioselectivity, suggesting that even with R3H, s-cis/s-trans rotamer control is satisfactory. Increasing the reaction temperature led to higher yield for 19 with a concomitant decrease in enantioselectivity (entry 5 in Table 1). In entries 6-8, electron withdrawing groups were found to enhance reactivity (reaction time: 1 h for 13 and 8 h for 11 at room temperature) with little impact on selectivity. Reactions with imides containing alkyl R4 substituents (15-17) gave higher selectivity as compared to aryl groups (entries 9, 10, and 14 in Table 1). When the magnesium counterion was varied (entries 11-13, 15-16 in Table 1), magnesium triflimide gave optimal enantio-selectivity. When temperature, imide R4, and chiral Lewis acid were all optimized (entries 9-16 in Table 1), the optimal substrate was determined to be 17, which gave 19 with outstanding levels of selectivity (96% ee and 96% de), as shown by entry 16 in Table 1, when magnesium triflimide was used as a Lewis acid. These results clearly demonstrate that a highly enantioselective method for the synthesis of α,β-disubstituted-β-amino acids (more particularly, α-monosubstituted-β-monosubstituted-β-amino acids) is at hand.
	With chiral 2,2'-cC₃H₄-bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole); magnesium bis(trifluoromethane solfonyl)imide In dichloromethane at -40℃;

Reference： [1]Current Patent Assignee: NDSU RESEARCH FOUNDATION - US2011/218342, 2011, A1 Location in patent: Page/Page column 11-12; 14-15
[2]Sibi, Mukund P.; Prabagaran, Narayanasamy; Ghorpade, Sandeep G.; Jasperse, Craig P. [Journal of the American Chemical Society, 2003, vol. 125, # 39, p. 11796 - 11797]

23
[ 622-30-0 ]
[ 146803-41-0 ]
C₂₅H₂₄N₂O₃ [ No CAS ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 3325 - 3334

24
[ 622-30-0 ]
[ 156939-62-7 ]
C₂₄H₂₂N₂O₃ [ No CAS ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 3325 - 3334

25
[ 123-11-5 ]
[ 622-30-0 ]
[ 115175-98-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene at 20℃; for 12h; Molecular sieve;
80%	In dichloromethane for 24h; Heating;
55%	With magnesium sulfate In dichloromethane at 20℃;

	at 20℃;
	With 4 A molecular sieve In toluene at 20℃;
726 mg	With sodium sulfate In dichloromethane for 18h; Inert atmosphere;
	With magnesium sulfate In diethyl ether at 20℃;
1.96 g	With sodium sulfate In dichloromethane at 20℃; for 18h; Inert atmosphere;

Reference： [1]Chandrasekhar; Ahn, Sewon; Ryu, Jae-Sang [Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6740 - 6749]
[2]Herrera; Nagarajan; Morales; Mendez; Jimenez-Vazquez; Zepeda; Tamariz; Tamariz [Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1252 - 1263]
[3]Evans, David A.; Song, Hyun-Ji; Fandrick, Keith R. [Organic Letters, 2006, vol. 8, # 15, p. 3351 - 3354]
[4]Kano, Taichi; Hashimoto, Takuya; Maruoka, Keiji [Journal of the American Chemical Society, 2005, vol. 127, # 34, p. 11926 - 11927]
[5]Sapeta, Katarina; Kerr, Michael A. [Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8597 - 8599]
[6]Pagoti, Sreenivasarao; Dutta, Debasish; Dash, Jyotirmayee [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3532 - 3538]
[7]Poulsen, Pernille H.; Vergura, Stefania; Monleón, Alicia; Jørgensen, Danny Kaare Bech; Jørgensen, Karl Anker [Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6412 - 6415]
[8]He, Chun-Ting; Han, Xiao-Li; Zhang, Yan-Xue; Du, Zhen-Ting; Si, Chang-Mei; Wei, Bang-Guo [Organic and Biomolecular Chemistry, 2021, vol. 19, # 2, p. 457 - 466]

26
[ 100-52-7 ]
[ 622-30-0 ]
[ 85225-56-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With magnesium sulfate In dichloromethane at 20℃; for 15h; Inert atmosphere;
92%	With magnesium sulfate In dichloromethane for 15h;
92%	With magnesium sulfate In dichloromethane for 24h;	1. General Procedure for Nitrone Preparation: General procedure: Amixture of hydroxylamine (1 mmol) or [hydroxylamine hydrochloride (1 mmol) and sodium bicarbonate (1.5 mmol)],aldehyde (1mmol), and anhydrous MgSO4(1.5 mmol) in either dichloromethane or ether was stirred till the consumption of the starting materials (confirmed by TLC analysis). Upon completion, the mixture was filtered and the filtrate concentrated in vacuo to yield the crude product, which was chromatographed on silica gel using ethyl acetate/hexane mixture as an eluant to afford the pure nitrones. (Z)-N-Benzylidene-benzylamine-N-oxide (A): 1A mixture of benzaldehyde (2.4 g, 19.5 mmol), N-benzyl-hydroxylamine (2 g, 18.8 mmol), and MgSO4 (2.5 g) were stirred in 100 ml CH2Cl2 for 24 h. Then the mixture was filtered and concentrated. Purification using chromatography on silica gelafforded 3.77 g (92%) (Z)-N-benzylidene-benzylamine-N-oxid. 1H NMR (500 MHz, CDCl3) δ 8.21 (br m, 2H), 7.49-7.40 (m, 9H), 5.05 (br, s, 2H); 13C NMR (125 MHz, CDCl3) δ 134.3, 133.2, 130.5, 129.2, 128.9, 128.6, 128.4, 71.2.

80%	In dichloromethane for 24h; Heating;
	With 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 20℃; for 2h; Inert atmosphere;	General procedure of synthesis of N-Benzyl fluoro nitrone in RTIL (1) General procedure: 2,6-difluoro benzaldehyde (1 mmol) and N-benzylhydroxylamine (1 equivalent) was added to [bmim]BF4 (2 mL) in a 10 ml conical flask, mixed thoroughly and stirred at room temperature for 2 hr. The formation of nitrone was monitored by TLC (Rf=0.40). After completion of reaction, the nitrone was washed with diethyl ether (3x10mL). The combined ether extracts were concentrated in vacuo and the nitrone was isolated as white crystalline solid (m.p 420C, uncorrected) As the nitrone decomposes on keeping at room temperature, in situ reactions were performed with alkynoids.
841 mg	With sodium sulfate In dichloromethane for 18h; Inert atmosphere;
	Stage #1: N-benzyl hydroxylalmine With sodium carbonate In methanol at 20℃; for 0.25h; Inert atmosphere; Stage #2: benzaldehyde In methanol at 20℃; for 16h; Inert atmosphere;
18.13 g	With sodium sulfate In dichloromethane at 20℃; for 18h; Inert atmosphere;

Reference： [1]Chandrasekhar; Ahn, Sewon; Ryu, Jae-Sang [Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6740 - 6749]
[2]Aschwanden, Patrick; Frantz, Doug E.; Carreira, Erick M. [Organic Letters, 2000, vol. 2, # 15, p. 2331 - 2333]
[3]Das, Prasanta; Hamme, Ashton T. [Tetrahedron Letters, 2017, vol. 58, # 12, p. 1086 - 1089]
[4]Herrera; Nagarajan; Morales; Mendez; Jimenez-Vazquez; Zepeda; Tamariz; Tamariz [Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1252 - 1263]
[5]Chakraborty, Bhaskar; Luitel, Govinda Prasad [Tetrahedron Letters, 2013, vol. 54, # 8, p. 765 - 770]
[6]Pagoti, Sreenivasarao; Dutta, Debasish; Dash, Jyotirmayee [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3532 - 3538]
[7]Cordier, Marie; Archambeau, Alexis [Organic Letters, 2018, vol. 20, # 8, p. 2265 - 2268]
[8]He, Chun-Ting; Han, Xiao-Li; Zhang, Yan-Xue; Du, Zhen-Ting; Si, Chang-Mei; Wei, Bang-Guo [Organic and Biomolecular Chemistry, 2021, vol. 19, # 2, p. 457 - 466]

27
[ 622-30-0 ]
[ 13304-62-6 ]

Reference： [1]Organic and biomolecular chemistry,2004,vol. 2,p. 1274 - 1276

28
[ 3010-05-7 ]
[ 622-30-0 ]

Reference： [1]Synthesis,2000,p. 1299 - 1304
[2]Organic Syntheses,2003,vol. 80,p. 207 - 218

29
[ 3849-01-2 ]
[ 622-30-0 ]
2,4,6-tris(N-benzylhydroxylaminomethyl)mesitylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 7 2,4,6-Tris(N-benzylhydroxylaminomethyl)mesitylene To a suspension of 3.87 g of sodium carbonate in 30 ml of dry N,N-dimethylformamide is added 4.50 g of N-benzylhydroxylamine followed by 3.23 g of 2,4,6-tris(chloromethyl)mesitylene. After stirring at 80 C. for 8 hours, dimethylformamide is removed under reduced pressure and the residue is partitioned between methylene chloride and water. The combined organic layers are washed with water, brine, dried and evaporated to give a crude product. Recrystallization from ethyl acetate-heptane affords 4.0 g of white solid, mp 193-195 C. Analysis: Calculated for C33 H39 N3 O3: C, 75.4; H, 7.5; N, 8.0. Found: C, 74.8; H, 7.4; N, 7.7.

Reference： [1]Patent: US4649221,1987,A

30
[ 7758-89-6 ]
[ 19790-60-4 ]
[ 622-30-0 ]
[ 2028-63-9 ]
[ 97363-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ammonia; In ethanol; hexane; water; ethyl acetate;	Example 1 1-Benzyl-4-(2-benzyloxyethyl)-3-(1-hydroxyethyl)azetidin-2-one To a solution of N-benzylhydroxylamine (3.1g) in ethanol (80ml), under argon, was added 3-benzyloxypropanal (4.45g). The clear solution was stirred for 30 min at ambient temperature and then a solution of butyn-3-ol in water (c 45%, 5ml) was added, followed by copper (I) chloride (3.5g) and concentrated aqueous ammonia (20ml). After stirring at ambient temperature for 2 hrs the mixture was added to hydrochloric acid (2M, 200ml), and then extracted with ethyl acetate (2 x 300ml). The organic extracts were combined and extracted with hydrochloric acid (2M, 100ml) and then saturated aqueous sodium chloride (2 x 100ml). The organic layer was dried over magnesium sulphate and evaporated to dryness. The residue was purified by mplc on silica using a gradient of ethyl acetate/hexane 1:4 changing linearly to ethyl acetate 100%. The appropriate fractions were evaporated to dryness to give 3.7g (44%) of a mixture of cis and trans isomers of the title compound as a clear oil. A sample of the cis isomer isolated as above had the following nmr in CDCl3 at 400 MHz: 1.45 (d, 3H); 1.8 (m, 1H); 2.1 (m, 1H); 3.2 (q, J = 5.5 and 11.0, 1H); 3.3 (m, 1H); 3.55 (m, 1H); 3.6 (m, 1H); 4.1 (m + d, 2H); 4.45, (s, 2H); 4.55 (d, 1H); 7.25 (m, 10H); M + H (FAB)=340.

Reference： [1]Patent: EP223588,1991,B1

31
[ 7758-89-6 ]
[ 74130-31-7 ]
[ 622-30-0 ]
[ 2028-63-9 ]
[ 112959-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In hydrogenchloride; ethanol; hexane; ethyl acetate;	Example 2 1-Benzyl-4-(2-benzyloxy-1-methylethyl)-3-(1-hydroxyethyl)azetidin-2-one 3-(Benzyloxy)-2-methylpropanal (3.60g) and N-benzylhydroxylamine (2.50g) were stirred together in 50ml ethanol under argon at ambient temperature for 45mins. To the resulting clear solution were added sequentially, while still stirring under argon, 5ml of a ca. 45% solution of butyn-3-ol, 3.0g of copper (I) chloride and 16ml concentrated aqueous ammonia. The pale green clear reaction mixture was stirred for 3hrs at ambient temperature under argon and then quenched in 200ml 2N hydrochloric acid, extracted with 2 x 300ml ethyl acetate and the organic extracts combined and washed with 2N hydrochloric acid (50ml), water (200ml) and saturated aqueous brine (100ml). Filtration through anhydrous sodium sulphate and evaporation in vacuo left 8.43g of a yellow oil. The residual oil was purified by mplc on silica using a 1:1 mixture of hexane/ethyl acetate to give 5.16g of the title compound as a near colourless oil (73%). Tlc on silica using hexane/ethyl acetate (1:1) as eluant showed two spots in approximately equal ratio of Rf's 0.12 and 0.15, which are the C3,4trans and cis isomers respectively. A sample of the cis isomer isolated as above had the following nmr in CDCl3: 0.98 (d, 3H); 1.45 (d, 3H); 1.70 (broad s, 1H); 2.45 (m, 1H); 3.18 (q, J = 5.5 and 10.5, 2H); 3.40 (q, 1H); 3.46 (q, 1H); 4.03 (d, 1H); 4.17 (sextet, 1H); 4.46 (s, 2M); 4.82 (d, 1H); 7.38 (m, 10H); M + H (CI)=354.

Reference： [1]Patent: EP223588,1991,B1

32
[ 7758-89-6 ]
aqueous diethanolamine [ No CAS ]
[ 74130-31-7 ]
[ 622-30-0 ]
[ 1423-60-5 ]
[ 112959-37-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	In ethanol; hexane; ethyl acetate;	Example 3 3-Acetyl-1-benzyl-4-(2-benzyloxy-1-methylethyl)trans-azetidin-2-one 3-(Benzyloxy)-2-methylpropanal (1.80g) and N-benzylhydroxylamine (1.35g) were stirred together in 40ml ethanol under argon at ambient temperature for 1hr. To the resulting clear soluton was added 1.40g copper (I) chloride and 4ml 50% aqueous diethanolamine. After 5mins (under argon), 0.80g (0.92ml) butyn-2-one was added dropwise in 5ml ethanol over ca. 20 mins, stirring under argon. After a further 2hrs the reaction mixture was poured into 100ml 2N hydrochloric acid and extracted with ethyl acetate (2 x 150ml). The organic extracts were washed sequentially with 2N hydrochloric acid, water and saturated brine and filtered through anhydrous sodium sulphate. Evaporation in vacuo gave 2.95g of a yellow oil. Purification by mplc using ethyl acetate/ hexane gave 2.07g of the title compound as a near colourless oil (58%). The material was single spot by tlc., silica;ethyl acetate/hexane 1:1, Rf 0.50. N.m.r. in CDCl3 0.90 (t, 3H); 2.04 (m, 1H); 2.20 (d, 3H, cis/trans isomers at C4,5); 3.23 (q, 1H); 3.33 (m, 1H); 3.89 (q, J = 2.5 and 6.5, part 1H, 1 isomer); 4.05 (m, 1.5H); 4.15 (d, part 1H, 1 isomer); 4.18 (m, 1H); 4.37 (unresolved d, 1H); 4.64 (q, 1H); 7.25 (m, 10H); M + H (CI)=352.

Reference： [1]Patent: EP223588,1991,B1

33
[ 498-66-8 ]
[ 622-30-0 ]
N-benzyl-N-exo-hydroxybicyclo[2.2.1]heptan-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium cyanoborohydride In propan-1-ol at 110℃; for 18h; Inert atmosphere; stereoselective reaction;

Reference： [1]Moran, Joseph; Gorelsky, Serge I.; Dimitrijevic, Elena; Lebrun, Marie-Eve; Bedard, Anne-Catherine; Seguin, Catherine; Beauchemin, Andre M. [Journal of the American Chemical Society, 2008, vol. 130, # 52, p. 17893 - 17906]

34
[ 2234-20-0 ]
[ 622-30-0 ]
[ 1093283-27-2 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 17893 - 17906

35
[ 1262039-14-4 ]
[ 622-30-0 ]
[ 1262039-17-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With titanium(IV) tetraethanolate In tetrahydrofuran at 70 - 80℃;	45 To a solution of 1-(3-bromophenyl)-3-(tert-butyldimethylsilyloxy)hex-5-en-1-one (6.84 g, 17.8 mmol) and N-benzylhydroxylamine (2.86 g, 23.2 mmol) in THF (60 mL) is added Ti(OEt)4 (8.14 g, 35.7 mmol). The reaction mixture is heated to 70° C. in a sealed tube. After 2 h, the temperature is increased to 80° C. and stirring is continued for 3 days. The reaction mixture is cooled to room temperature. Water and ethyl acetate are added and the mixture is stirred vigorously for 15 minutes. The solids are allowed to settle and the organic and aqueous layers are decanted through a pad of diatomaceous earth. The layers are separated and the aqueous layer is extracted three times with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with 0% to 20% ethyl acetate in hexanes gradient over 20 minutes to give the title compound as a diastereomeric mixture (7.42 g, 85%). ES/MS m/e (79Br/81Br) 488, 490 (M+1).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; ELI LILLY & CO - US2011/9395, 2011, A1 Location in patent: Page/Page column 24

36
[ 29601-98-7 ]
[ 622-30-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydrogencarbonate In water	A solution of N-(phenylmethyl)hydroxylamine hydrochloride (Fluorochem, cat n° 091512) (10.5g, 65.79mmol) in water (54mL) was treated with NaHCCh (10.5g, l24.99mmol) and extracted with DCM (l00mLX3). The water phase was further basified with 2N NaOH until rH=10 (by paper) and extracted with EtOAc. The combined organic extracts were dried over Na2S04 (anh.), filtered and evaporated giving N-benzylhydroxylamine (8.l0g, 65.79mmol, yield quantitative) asa low melting white solid. Method 1; Rt: 0.66 m/z: 124.00 (M+H)+.
	With sodium hydrogencarbonate In methanol for 0.25h;
	With 4-methyl-morpholine In dichloromethane Schlenk technique; Inert atmosphere;

Reference： [1]Current Patent Assignee: ANTIOS THERAPEUTICS - WO2020/30781, 2020, A1 Location in patent: Page/Page column 54; 56
[2]Location in patent: experimental part Collin, Marie-Pierre; Vasella, Andrea [Helvetica Chimica Acta, 2010, vol. 93, # 12, p. 2297 - 2317]
[3]Marchi, Luciano; Marchetti, Nicola; Atzeri, Corrado; Borghesani, Valentina; Remelli, Maurizio; Tegoni, Matteo [Dalton Transactions, 2015, vol. 44, # 7, p. 3237 - 3250]

37
[ 25581-41-3 ]
[ 622-30-0 ]
[ 717920-96-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: D-erythronolactone acetonide; N-benzyl hydroxylalmine In dichloromethane at 25℃; for 0.5h; Stage #2: With trimethylaluminum In hexane; dichloromethane at 25℃; for 3.33333h; Cooling with ice;	(4R,5R)-5-(Hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide (8) To a stirring solution of 2,3-O-isopropylidene-D-erythronolactone (7; 1.8g, 11.4mmol) at 25 °C in 25mL of dichloromethane was added N-hydroxybenzylamine (1.54g, 12.5mmol). After 30 min at 25 °C, the mixture was cooled in an ice bath and trimethylaluminum (2M in hexane; 8.25mL, 16.5mmol) was added over a period of 10 min. After frothing had subsided, the ice bath was removed and the mixture stirred at 25 °C for 2.5 h. The mixture was poured into 150mL of 5% aq NaHCO3, stirred for 10 min after the initial frothing had subsided, and then filtered through Celite rinsing thoroughly with dichloromethane.The filtrate was allowed to stratify, and then the layers were separated and the organic phase dried over anhydr. MgSO4. Concentration of the solvent left an oil that solidified almost immediately to leave 2.56 g of white flakes (mp 103-110°C) which were triturated in 10-15mL of diethyl ether and then stirred at 25 °C for several hours.The solid was collected, rinsed with ether and dried under reduced pressure to afford2.10g (66%) of 8 asa snow-white crystalline powder: mp 119-121°C (lit7 111-112 °C); one spot by TLC[EtOAc/hexane 1:1]; 1HNMR was the same as previously reported7 and consistent with the desired product in high purity.

Reference： [1]Yep, Alejandra; Sorenson, Roderick J.; Wilson, Michael R.; Hollis Showalter; Larsen, Scott D.; Keller, Paul R.; Woodard, Ronald W. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2679 - 2682]

38
[ 622-30-0 ]
[ 613672-38-1 ]
[ 613672-40-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With magnesium bis(trifluoromethane solfonyl)imide In dichloromethane at -40℃; Inert atmosphere;	1.12 Our experiments began with addition of N-benzyl hydroxylamine to tiglates (8-17) with different achiral templates using catalytic amounts (5-30 mol %) of a chiral Lewis acid derived from ligand 18 and magnesium salts, as shown in Table 1. That the same isoxazolidinone product formed regardless of template streamlined our assessment of enantioselectivity. Results from these studies are also shown in Table 1. TABLE 1 EntrySMa R3 R4 Lewis Acid T ° C.Yieldb dec eed 1 8-CH2CH2CH2-Mg(ClO4)2 -40 10 95 70 2 9-CH2CH2O-Mg(ClO4)2 -40 8 95 40 3 10 Me PhMg(ClO4)2 -40 10 60 18 4 11 H PhMg(ClO4)2 -40 47 94 75 5 11 H PhMg(ClO4)2 25 66 90 45 6 12 H3,5-(CF3)2-PhMg(ClO4)2 25 70 92 40 7 13 H3,5-(NO2)2-PhMg(ClO4)2 25 66 90 44 8 14 H4-NO2-PhMg(ClO4)2 25 62 94 46 9 15 H t-butylMg(ClO4)2 25 45 92 57 10 16 H cyclohexylMg(ClO4)2 25 64 88 67 11 16 H cyclohexylMg(ClO4)2 -40 76 92 88 12 16 H cyclohexylMg(Ntf2)2 -40 66 90 96 13 16 H cyclohexylMgI2 -40 62 90 70 14 17 H i-propylMg(ClO4)2 25 78 94 54 15 17 H i-propylMg(ClO4)2 -40 76 96 90 16 17 H i-propylMg(Ntf2)2 -40 72 96 96 aSM = starting materialbisolated yield after column chromatographycdiastereomeric excess determined by 1H-NMR (500 MHz)ddetermined by chiral HPLCConjugate amine addition to pyrrolidinone (8) or oxazolidinone (9) derived tiglate gave low yields, although the diastereoselectivity and enantioselectivity were good (entries 1 and 2 in Table 1). With regard to diastereoselectivity, the major diastereomer of 18 had trans stereochemistry for the substituents as established by NMR. This is believed to be a consequence of the syn addition of the amine to the substrate in a concerted manner. Reaction with tertiary imide 10 (R3=CH3) was also very slow and low-yielding, and this reaction gave 19 with low selectivity (entry 3 in Table 1). By contrast, secondary imides 11-17 (R3=H), lacking the A1,3 strain present in 8-10, were much more reactive and gave good yields. Our initial attempt with benzimide 11 (entry 4 in Table 1) gave excellent diastereoselectivity and good enantioselectivity, suggesting that even with R3H, s-cis/s-trans rotamer control is satisfactory. Increasing the reaction temperature led to higher yield for 19 with a concomitant decrease in enantioselectivity (entry 5 in Table 1). In entries 6-8, electron withdrawing groups were found to enhance reactivity (reaction time: 1 h for 13 and 8 h for 11 at room temperature) with little impact on selectivity. Reactions with imides containing alkyl R4 substituents (15-17) gave higher selectivity as compared to aryl groups (entries 9, 10, and 14 in Table 1). When the magnesium counterion was varied (entries 11-13, 15-16 in Table 1), magnesium triflimide gave optimal enantio-selectivity. When temperature, imide R4, and chiral Lewis acid were all optimized (entries 9-16 in Table 1), the optimal substrate was determined to be 17, which gave 19 with outstanding levels of selectivity (96% ee and 96% de), as shown by entry 16 in Table 1, when magnesium triflimide was used as a Lewis acid. These results clearly demonstrate that a highly enantioselective method for the synthesis of α,β-disubstituted-β-amino acids (more particularly, α-monosubstituted-β-monosubstituted-β-amino acids) is at hand.

Reference： [1]Current Patent Assignee: NDSU RESEARCH FOUNDATION - US2011/218342, 2011, A1 Location in patent: Page/Page column 11-12; 14-15

39
[ 1333397-31-1 ]
[ 622-30-0 ]
C₁₇H₂₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With magnesium bis(trifluoromethane solfonyl)imide In dichloromethane at -40℃; for 24h;	3 Conjugate addition on cyclopentene carboxylates was carried out to produce 53 from imide 52 as described in Table 4. TABLE 4 Entry R Lewis Acid time (h) T ° C. Yield de ee 1 isopropylMg(ClO4)2 24 -40 90 >95 84 2 cyclohexylMg(ClO4)2 24 -40 75 >95 79 3 isopropylMg(NTf2)2 24 -40 90 >95 94 4 cyclohexylMg(NTf2)2 24 -40 78 >95 90 Good reaction rates and excellent selectivities were observed. The isopropyl template was found to be better than the cyclohexyl template, and the use of Mg(NTf2)2 produced better enantioselectivities than Mg(ClO4)2. Catalytic hydrogenation of 53 produces β-amino acid 54.

Reference： [1]Current Patent Assignee: NDSU RESEARCH FOUNDATION - US2011/218342, 2011, A1 Location in patent: Page/Page column 18

40
[ 627-37-2 ]
[ 622-30-0 ]
N2-benzyl-N2-hydroxy-N1-methylpropane-1,2-diamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16571 - 16577,7
[2]Organic Letters,2012,vol. 14,p. 5082 - 5085,4
[3]Journal of the American Chemical Society,2011,vol. 133,p. 20100 - 20103

41
[ 59717-69-0 ]
[ 622-30-0 ]
[ 1349708-36-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With formaldehyd In <i>tert</i>-butyl alcohol at 30℃; for 24h; Inert atmosphere;
56%	With benzyloxyacetoaldehyde In benzene at 60℃; for 29h; Inert atmosphere;

Reference： [1]Guimond, Nicolas; MacDonald, Melissa J.; Lemieux, Valerie; Beauchemin, Andre M. [Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16571 - 16577,7]
[2]MacDonald, Melissa J.; Schipper, Derek J.; Ng, Peter J.; Moran, Joseph; Beauchemin, Andre M. [Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20100 - 20103]

42
[ 622-30-0 ]
[ 107-11-9 ]
[ 1349708-32-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: N-benzyl hydroxylalmine; 1-amino-2-propene With benzyloxyacetoaldehyde In chloroform at 20℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; chloroform; water at 20℃; for 1h; Inert atmosphere; Stage #3: With sodium carbonate In water
71%	With benzyloxyacetoaldehyde In benzene at 25℃; for 24h; Inert atmosphere;
56%	In neat (no solvent) at 80℃; for 17h; Inert atmosphere; regioselective reaction;

Reference： [1]MacDonald, Melissa J.; Schipper, Derek J.; Ng, Peter J.; Moran, Joseph; Beauchemin, Andre M. [Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20100 - 20103]
[2]Guimond, Nicolas; MacDonald, Melissa J.; Lemieux, Valerie; Beauchemin, Andre M. [Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16571 - 16577,7]
[3]Zhao, Shu-Bin; Bilodeau, Eric; Lemieux, Valerie; Beauchemin, Andre M. [Organic Letters, 2012, vol. 14, # 19, p. 5082 - 5085,4] Zhao, Shu-Bin; Bilodeau, Eric; Lemieux, Valérie; Beauchemin, André M. [Organic Letters, 2012, vol. 14, # 19, p. 5082 - 5085]

43
[ 622-30-0 ]
[ 124-02-7 ]
[ 1349708-34-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With formaldehyd In <i>tert</i>-butyl alcohol at 30℃; for 24h; Inert atmosphere;
69%	With benzyloxyacetoaldehyde In benzene at 20℃; for 24h; Inert atmosphere;

Reference： [1]Guimond, Nicolas; MacDonald, Melissa J.; Lemieux, Valerie; Beauchemin, Andre M. [Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16571 - 16577,7]
[2]MacDonald, Melissa J.; Schipper, Derek J.; Ng, Peter J.; Moran, Joseph; Beauchemin, Andre M. [Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20100 - 20103]

44
(2R,4'R)-ethyl 2-[2'-(p-bromophenyl)-1',3'-dioxolan-4'-yl]-2-(tert-butyldimethylsiloxy)ethanoate [ No CAS ]
[ 622-30-0 ]
(Z)-N-benzyl-N-(2S,4'R)-{2-[2'-(p-bromophenyl)-1',3'-dioxolan-4'-yl]-2-(tert-butyldimethylsiloxy)ethyliden}aminoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: (2R,4'R)-ethyl 2-[2'-(p-bromophenyl)-1',3'-dioxolan-4'-yl]-2-(tert-butyldimethylsiloxy)ethanoate With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 3.5h; Inert atmosphere; Stage #2: N-benzyl hydroxylalmine With magnesium sulfate In dichloromethane at 20℃;	Analogous to the literature [3], ester 2 (5.00 g, 11.2 mmol, d.r. 83:17) was dissolvedin dry CH2Cl2 (22 mL) and the solution was cooled to -78 °C under argon atmosphere. DIBAL-H (80% in toluene, 9.8 mL) was added dropwise. After stirringthe reaction mixture for 3.5 h at that temperature, an aq solution of potassium sodiumtartrate (40 mL) was added and the emulsion was stirred for 2.5 h. The resulting twophases were separated and the aq layer was extracted with CH2Cl2 (3 × 35 mL). Thecombined organic layers were washed with brine, dried with Na2SO4, filtered throughcotton and the solvent was removed in vacuo to give the aldehyde (4.51 g, 11.2 mol,d.r. 86:14) as a colorless liquid that was used without purification for the next step.The aldehyde was dissolved in CH2Cl2 (71 mL). Afterwards, MgSO4 (3.64 g, 30.2mmol) and N-benzylhydroxylamine (3.18 g, 25.9 mmol) were added and the resultingslightly yellow mixture was stirred at rt overnight. The reaction mixture was thenfiltered through cotton and the solvent was removed in vacuo. The obtained crudematerial (yellow oil, 12.3 g) was purified by column chromatography (silica gel,hexanes/EtOAc 3:1) to yield nitrone 3 (4.70 g, 83% over 2 steps, d.r. 86:14) as ayellow oil; [α]D22 +13.1 (c 0.85, CHCl3); TLC [silica gel, hexanes/EtOAc = 1:2] Rf 0.68;Signals of the major diastereomer are assigned with : 1H NMR (500 MHz, CDCl3): δ-0.04 (s, 3 H, SiMe), -0.01 (s, 3 H, SiMe), 0.04 (s, 3 H, SiMe), 0.09 (s, 3 H, SiMe),0.82 (s, 9 H, Sit-Bu), 0.85 (s, 9 H, Sit-Bu), 3.96-4.00 (m, 2 H, 5’-H, 5’-H), 4.05-4.10(m, 2 H, 5’-H, 5’-H), 4.35 (dt, J ≈ 4.9, 7.2 Hz, 1 H, 4’-H), 4.43* (dt, J ≈ 4.8, 6.6 Hz, 1H, 4’-H), 4.84, 4.85 (AB system, JAB = 13.6 Hz, 1 H each, NCH2), 4.89 (s, 2 H,NCH2), 5.13 (dd, J = 4.9, 6.8 Hz, 1 H, 2-H), 5.20 (dd, J = 4.8, 6.1 Hz, 1 H, 2-H),5.59 (s, 1 H, 2’-H), 5.85 (s, 1 H, 2’-H), 6.62 (d, J = 6.8 Hz, 1 H, 1-H), 6.63 (d, J = 6.1Hz, 1 H, 1-H), 7.29 (AB part of AA’BB’ system, JAB = 8.4 Hz, 2 H, Ar), 7.32 (AB partof AA’BB’ system, JAB = 8.4 Hz, 2 H, Ar), 7.33-7.39 (m, 5 H, Ph), 7.40 (s, 5 H, Ph),4.46 (A’B’ part of AA’BB’ system, JA’B’ = 8.4 Hz, 2 H, Ar), 4.48 (A’B’ part of AA’BB’system, JA’B’ = 8.4 Hz, 2 H, Ar) ppm; 13C NMR (125 MHz, CDCl3): δ -5.0, -4.9, -4.8,-4.7 (4 q, SiMe, SiMe), 18.1¥, 25.8¥ (s, q, SiCMe3, SiCMe3), 66.7, 66.8 (2 t, C-5’,C-5’), 67.3 (d, C-2), 68.1 (d, C-2), 70.15 (t, NCH2), 70.20 (t, NCH2), 76.8 (d, C-4’), 78.1 (d, C-4’), 103.8 (d, C-2’), 103.9 (d, C-2’), 123.4, 123.5 (2 s, Ar, Ar), 128.4,128.7, 129.1, 129.2, 129.3, 129.4, 129.46, 129.49 (8 d, Ar, Ar, Ph, Ph), 131.5,131.6 (2 d, Ph, Ph), 132.4, 132.5, 136.1, 137.0 (4 s, Ar, Ar, Ph, Ph), 137.7, 137.8(2 d, C-1, C-1) ppm; ¥overlapping of 2 signals; the signals of the diastereomercould not be assigned; IR (ATR) ~ : 3085-3030 (=C-H), 2950-2855 (C-H), 1690-1560(C=C, C=N), 1280 (N-O), 1255 (C-O) cm-1; ESI-TOF (m/z): [M + Na]+ calcd forC24H32BrNO4SiNa, 528.1176; found 528.1158

Reference： [1]Bouche, Lea; Kandziora, Maja; Reissig, Hans-Ulrich [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 213 - 223]

45
[ 622-30-0 ]
[ 148992-43-2 ]
N-benzyl C-(difluoromethyl)nitrone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With toluene-4-sulfonic acid In toluene for 0.1h; Dean-Stark; Reflux;	N-Benzyl C-(difluoromethyl)nitrone (1b). Difluoroacetaldehydeethyl hemiacetal (819 mg, 6.5 mmol) was added to a solution offreshly prepared N-benzyl hydroxylamine (615 mg, 5 mmol) and acatalytic amount of p-TsOHH2O (19 mg, 0.1 mmol) in toluene(10 ml). The mixture was heated at reflux in a Dean-Starkapparatus until evolution of water was finished (ca. 1 h), andthen the solvent was evaporated. Pure product was obtained aftercrystallization from hexane 894 mg (84%), m.p. 60-62 8C (hexane).1H NMR (600 MHz, CDCl3): d 4.97 (s, 2H, CH2), 6.72 (td,2JH,F = 53.4 Hz, 3JH,H = 5.4 Hz, 1H, CH), 6.88 (td, 3JH,F = 3JH,H = 5.4 Hz,1H, CHF2), 7.43-7.48 (m, 5 arom. CH). 13C NMR (150 MHz, CDCl3): d70.7 (CH2), 108.7 (t, 1JC,F = 231.3 Hz, CHF2), 130.0 (t, 2JC,F = 35.4 Hz,CH), 129.3, 129.6, 129.7 (5 arom. CH), 131.2 (1 arom. C). 19F NMR(565 MHz, CDCl3): d 121.6 (dd, 2JH,F = 53.4 Hz, 3JH,H = 5.4 Hz, 2F,CHF2). IR (KBr): v 3184w, 3090s, 3036m, 1597vs (C55N), 1459vs,1434s, 1307s, 1200s, 1212s, 1119vs, 1042vs, 932m, 908m, 706vs.HR-ESI-MS: 208.05428 (208.05444 calcd. for C9H9F2NNaO,[M+Na]+).
	With toluene-4-sulfonic acid In toluene for 0.5h; Reflux; Dean-Stark;

Reference： [1]Mlostoń, Grzegorz; Obijalska, Emilia; Celeda, Małgorzata; Mittermeier, Verena; Linden, Anthony; Heimgartner, Heinz [Journal of Fluorine Chemistry, 2014, vol. 165, p. 27 - 32]
[2]Kowalski, Marcin K.; Mlostoń, Grzegorz; Obijalska, Emilia; Linden, Anthony; Heimgartner, Heinz [Tetrahedron, 2016, vol. 72, # 35, p. 5305 - 5315]

46
[ 104-88-1 ]
[ 622-30-0 ]
[ 22687-09-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyrrolidine In dichloromethane at 20℃; for 0.05h;
	Inert atmosphere;

Reference： [1]Morales, Sara; Guijarro, Fernando G.; Alonso, Inés; García Ruano, José Luis; Cid, M. Belén [ACS Catalysis, 2016, vol. 6, # 1, p. 84 - 91]
[2]Zhang, Ming; Kumagai, Naoya; Shibasaki, Masakatsu [Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12450 - 12455]

47
[ 622-30-0 ]
[ 251948-88-6 ]
tert-butyl 1-benzyltetrahydro-1H-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: N-benzyl hydroxylalmine With magnesium bromide In dichloromethane for 0.25h; Stage #2: N-allyl-N-(tert-butyloxycarbonyl)-glycinal With isopropyl alcohol In dichloromethane at 35℃; for 3h;	4.5 Step 5: Synthesis of tert-butyl l-benzyltetrahydro-lH-pyrrolo[3,4-c]isoxazole-5(3H)- carboxylate To a suspension of N-benzylhydroxylamine (1.33 g, 10 mmol) in DCM (40 mL) was added MgBr2 (2 g, 10 mmol). After stirring the mixture for 15 min, 2-propanol (0.65g, 10 mmol) was added and after stirring for an additional 10 min. a solution of tert- butyl allyl(2-oxoethyl)carbamate (1.8 g, 9 mmol) in DCM (10 mL) was added. The mixture was stirred at 35 °C for 3 hrs, poured into 5% aqueous NaHC03/ice and extracted with DCM. The combined organic extract was washed with water, brine, dried over Na2S04 and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate-hexanes 1 :4, to yield tert-butyl 1- benzyltetrahydro-lH-pyrrolo[3,4-c]isoxazole-5(3H)-carboxylate as an oil (1.8 g, 66%). 1H NMR (400 MHz, CDC13): δ 7.40-7.30 (m, 5H), 4.25 (s, 1H), 4.15-3.24 (m, 9H), 1.46 (s, 9H); LCMS: m/z = 305.2 [M+H]+

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2016/40504, 2016, A1 Location in patent: Paragraph 0203

48
[ 2058-72-2 ]
[ 622-30-0 ]
C₁₆H₁₃BrN₂O₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3759 - 3764

49
[ 667463-64-1 ]
[ 622-30-0 ]
C₁₆H₁₃BrN₂O₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3759 - 3764

50
[ 622-30-0 ]
[ 102-92-1 ]
N-benzylcinnamohydroxamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate In diethyl ether; water at 5℃;	Synthesis of N-benzyl cinnamohydroxamic acid (1b) N-benzyl hydroxyl amine (0.1 mol) was coupled with ethereal solution (50 mL) of cinnamoyl chloride (0.1 mol) in the presenceof saturated aqueous solution of sodium carbonate (0.1 mol) on the magnetic stirrer. Keep the temperature below than 5 °C during the reaction and recrystallize with chloroform and petroleum ether white shining N-benzyl cinnamohydroxamicacid (1b) was obtained [23] (Fig. 2).

Reference： [1]Rajput, Surendra K.; Patel, Anita; Bapat, Kishor N. [Asian Journal of Chemistry, 2017, vol. 29, # 4, p. 885 - 887]

51
[ 621-07-8 ]
[ 622-30-0 ]

Reference： [1]Asian Journal of Chemistry,2017,vol. 29,p. 885 - 887

52
[ 2058-72-2 ]
[ 622-30-0 ]
C₁₆H₁₃BrN₂O₂ [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2017,vol. 35,p. 857 - 860

53
[ 667463-64-1 ]
[ 622-30-0 ]
C₁₆H₁₃BrN₂O₂ [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2017,vol. 35,p. 857 - 860

54
[ 622-30-0 ]
[ 62-53-3 ]
[ 87-13-8 ]
ethyl 2-benzyl-5-hydroxy-3-(phenylamino)-2,3-dihydroisoxazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: N-benzyl hydroxylalmine; diethyl 2-ethoxymethylenemalonate With pyridine at 85℃; for 4h; Stage #2: aniline With potassium carbonate In ethyl acetate at 20℃;	Cascade Synthesis of Compounds 3 General procedure: To a mixture of diethyl 2-(ethoxymethylene)malonate (4) (0.6 mmol) and hydroxylamine 5 (0.6 mmol) was added pyridine (0.1 mmol), andthe resulting mixture was stirred at 85 °C for 4 h. After cooling the reaction mixture to r.t., amine 2 (0.5 mmol), K2CO3 (0.5 mmol or 1.0mmol) and EtOAc (3 mL) were added. The mixture was stirred at r.t. until the reaction was complete (as detected by TLC monitoring). The insoluble salt (K2CO3) was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EtOAc, 10:1 to 4:1) to afford the desired product 3.

Reference： [1]Li, Runrun; Wei, Qiang; Wang, Xin; Ge, Zemei; Li, Runtao [Synthesis, 2017, vol. 49, # 18, p. 4341 - 4349]

55
[ 105-76-0 ]
[ 24680-50-0 ]
[ 622-30-0 ]
dibutyl (3S,4R,5S)-2-benzyl-3-((E)-4-methoxystyryl)isoxazolidine-4,5-dicarboxylate [ No CAS ]
C₂₉H₃₇NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: An oven dried 4 mL vial, substituted enal (0.5 mmol, 1 equiv.) and N-benzylhydroxylamine (0.51 mmol, 1.01 equiv.) were dissolved in dichloroethane (1 mL). The resulting mixture is then stirred at room temperature for 2h. Dipolarophile (1 mmol, 2 equiv.) was then added and the resulting mixture was heated at 80C for 12 hours or until nitrone is fully consumed by TLC. The resulting crude is dried under pressure and the residue was loaded directly onto a silica gel column for purification.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4682 - 4686

56
[ 15933-07-0 ]
[ 622-30-0 ]
(E)-N-(1-ethoxy-1-oxobutan-2-ylidene)-1-phenylmethanamine oxide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6763 - 6774

57
[ 89598-96-9 ]
[ 622-30-0 ]
[ 213814-61-0 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9456 - 9460
Angew. Chem.,2018,vol. 130,p. 9600 - 9604,5

58
[ 622-30-0 ]
[ 177490-82-3 ]
4-(benzylamino)phenyl acetate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9456 - 9460
Angew. Chem.,2018,vol. 130,p. 9600 - 9604,5

59
[ 24067-17-2 ]
[ 622-30-0 ]
[ 14309-92-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With trichloroacetonitrile In <i>tert</i>-butyl alcohol at 28℃;

Reference： [1]Sun, Hong-Bao; Gong, Liang; Tian, Yu-Biao; Wu, Jin-Gui; Zhang, Xia; Liu, Jie; Fu, Zhengyan; Niu, Dawen [Angewandte Chemie - International Edition, 2018, vol. 57, # 30, p. 9456 - 9460][Angew. Chem., 2018, vol. 130, # 30, p. 9600 - 9604,5]

60
[ 71597-85-8 ]
[ 622-30-0 ]
[ 103-14-0 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9456 - 9460
Angew. Chem.,2018,vol. 130,p. 9600 - 9604,5

61
[ 622-30-0 ]
[ 331834-13-0 ]
N-benzylbenzofuran-5-amine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9456 - 9460
Angew. Chem.,2018,vol. 130,p. 9600 - 9604,5

62
[ 88496-88-2 ]
[ 622-30-0 ]
[ 46120-25-6 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9456 - 9460
Angew. Chem.,2018,vol. 130,p. 9600 - 9604,5

63
[ 849052-26-2 ]
[ 622-30-0 ]
[ 32861-52-2 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9456 - 9460
Angew. Chem.,2018,vol. 130,p. 9600 - 9604,5

64
tert-butyl 3-(4-methoxyphenyl)-2-oxobutanoate [ No CAS ]
[ 622-30-0 ]
(E)-N-benzyl-1-(tert-butoxy)-3-(4-methoxyphenyl)-1-oxobutan-2-imine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In <i>tert</i>-butyl alcohol at 85℃; for 48h;	Nitrones 2; General Procedure General procedure: The α-keto ester (0.500 mmol) and N-benzylhydroxylamine (1.50mmol) were combined neat in a flame-dried reaction tube equippedwith a stir bar. tBuOH (1.52 mL) was added and the reaction mixturewas sealed and heated at 85 °C for 48 h. Upon complete consumptionof the starting α-keto ester, as indicated by TLC (staining with CAM),the reaction mixture was concentrated and purified by silica gel columnchromatography.

Reference： [1]Bartlett, Samuel L.; Keiter, Kimberly M.; Zavesky, Blane P.; Johnson, Jeffrey S. [Synthesis, 2019, vol. 51, # 1, p. 203 - 212]

65
[ 622-30-0 ]
t-butyl 2-oxo-4-phenylbutanoate [ No CAS ]
(E)-N-benzyl-1-(tert-butoxy)-1-oxo-4-phenylbutan-2-imine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In <i>tert</i>-butyl alcohol at 85℃; for 48h;	Nitrones 2; General Procedure General procedure: The α-keto ester (0.500 mmol) and N-benzylhydroxylamine (1.50mmol) were combined neat in a flame-dried reaction tube equippedwith a stir bar. tBuOH (1.52 mL) was added and the reaction mixturewas sealed and heated at 85 °C for 48 h. Upon complete consumptionof the starting α-keto ester, as indicated by TLC (staining with CAM),the reaction mixture was concentrated and purified by silica gel columnchromatography.

Reference： [1]Bartlett, Samuel L.; Keiter, Kimberly M.; Zavesky, Blane P.; Johnson, Jeffrey S. [Synthesis, 2019, vol. 51, # 1, p. 203 - 212]

66
tert-butyl 2-oxo-3-(pyridin-3-yl)butanoate [ No CAS ]
[ 622-30-0 ]
(E)-N-benzyl-1-(tert-butoxy)-1-oxo-3-(pyridin-3-yl)butan-2-imine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In <i>tert</i>-butyl alcohol at 85℃; for 48h;	Nitrones 2; General Procedure General procedure: The α-keto ester (0.500 mmol) and N-benzylhydroxylamine (1.50mmol) were combined neat in a flame-dried reaction tube equippedwith a stir bar. tBuOH (1.52 mL) was added and the reaction mixturewas sealed and heated at 85 °C for 48 h. Upon complete consumptionof the starting α-keto ester, as indicated by TLC (staining with CAM),the reaction mixture was concentrated and purified by silica gel columnchromatography.

Reference： [1]Bartlett, Samuel L.; Keiter, Kimberly M.; Zavesky, Blane P.; Johnson, Jeffrey S. [Synthesis, 2019, vol. 51, # 1, p. 203 - 212]

67
C₃₀H₄₀N₄O₁₀S [ No CAS ]
[ 622-30-0 ]
benzyl tert-butyl ((S)-5-(((3R,5R)-5-((benzyloxy)carbamoyl)-1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)amino)-5-oxopentane-1,4-diyl)dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 72h;	1.1.Benzyl tert-butyl ((S)-5-(((3R,5R)-5-((benzyloxy)carbamoyl)-1-((4-methoxyphenyl)sulfonyl) pyrrolidin-3-yl)amino)-5-oxopentane-1,4-diyl)dicarbamate(17) To the solution of compound 15 (210 mg, 0.32 mmol) in THF (900 μL),a 1M aqueous solution of LiOH (600 µL) was added dropwise at 0 °C. The solutionwas left reacting at room temperature for 1 h, then, it was taken up in 1M HCl, extracted with EtOAc, dried overanhydrous Na2SO4, filtered, and concentrated underreduced pressure. The crude residue was dissolved in dichloromethane (3mL), successively at 0 ° C, benzyl-hydroxylamine (76 mg, 0.48 mmol), HOBt (47mg, 0.35 mmol), EDC.HCl (67 mg, 0.35 mmol) and triethylamine (132µL, 0.95 mmol) were added in sequence. The reaction was left reacting at roomtemperature for 72 h, successively the mixture was diluted with dichloromethaneand washed with 1M HCl, a saturated solution of NaHCO3 and brine.The organic solution was dried over Na2SO4, concentratedunder reduced pressure and purified by flash chromatography (Petr.Et. / EtOAc =1 : 1) to give the pure product as a yellow oil in an overall yield of 75%,over two steps. [α]D22 =-19.2 (CHCl3, c = 1.1). 1HNMR (400 MHz, CDCl3) δ 7.80 (br s, 1H), 7.77 (d, J = 8.9 Hz, 2H), 7.75 - 7.62 (m, 10H),6.93 (d, J = 8.9 Hz, 2H), 5.37 - 5.20 (m, 2H), 5.02 (s,2H), 4.90 (dd, J = 29.7, 10.9 Hz,2H), 4.28 (br s, 1H), 4.07 (t, J = 17.2 Hz, 2H), 3.84 (s, 3H), 3.40 -3.24 (m, 2H), 3.16 (d, J = 5.9 Hz, 2H), 2.08 (t, J = 17.7 Hz, 2H), 1.94 - 1.81 (m, 1H), 1.83-1.69 (m, 1H), 1.68 -1.45 (m, 1H), 1.40 (s, 10H). 13C NMR (100 MHz, CHCl3) δ171.8, 169.0, 163.7, 156.6, 155.5, 136.6, 134.8, 132.1, 129.9 (2C), 129.3,128.7 (2C), 128.6, 128.4 (2C), 127.9 (2C), 127.9, 126.9, 114.6 (2C), 79.8,78.4, 66.4, 59.0, 55.6, 55.1, 53.7, 48.8, 40.3, 34.6, 30.2, 28.3 (3C), 25.6. MS (ESI) m/z (%) = 776.41 (100, [M +Na]+).

Reference： [1]Contini, Alessandro; Lenci, Elena; Trabocchi, Andrea [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 20]

68
C₃₁H₄₂N₄O₁₀S [ No CAS ]
[ 622-30-0 ]
benzyl tert-butyl ((S)-6-(((3R,5R)-5-((benzyloxy)carbamoyl)-1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)amino)-6-oxohexane-1,5-diyl)dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h;	1.1. Benzyl tert-butyl((S)-6-(((3R,5R)-5-((benzyloxy) carbamoyl)-1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)amino)-6-oxohexane-1,5-diyl)dicarbamate (18) To the solution of compound 16 (340 mg, 0.50 mmol) in THF (2 mL), a1M aqueous solution of LiOH (900 µL) was added dropwise at 0 °C. The solutionwas left reacting at room temperature for 1 h, then, it was taken up in 1M HCl, extracted with EtOAc, dried overanhydrous Na2SO4, filtered, and concentrated underreduced pressure. The crude residue was dissolved in dichloromethane (1.6mL), successively at 0 ° C, benzyl-hydroxylamine (88 mg, 0.55 mmol), HOBt (68mg, 0.55 mmol), EDC.HCl (105 mg, 0.55 mmol) and triethylamine (208µL, 1.50 mmol) were added in sequence. The reaction was left reacting at roomtemperature for 72 h, successively the mixture was diluted with dichloromethaneand washed with 1M HCl, a saturated solution of NaHCO3 and brine.The organic solution was dried over Na2SO4, concentratedunder reduced pressure and purified by flash chromatography (Petr.Et. / EtOAc =1 : 1) to give the pure product as a yellow oil in an overall yield of 57% ,over two steps. [α]D22 =+ 27.3 (CHCl3, c = 0.7). 1HNMR (400 MHz, CDCl3) δ 7.78 (d,J = 8.9 Hz, 2H), 7.50 - 7.30(m, 10H), 6.99 (d, J = 8.9 Hz, 2H), 5.21 (br s, 2H), 5.07 (s, 2H),4.92 (dd, J = 29.3, 10.9 Hz, 2H),4.31 (br s, 1H), 4.07 - 3.96 (m, 1H), 3.86 (s, 3H), 3.37 - 3.20 (m, 2H), 3.20 -3.02 (m, 2H), 2.13 (d, J = 13.8 Hz,1H), 1.94 - 1.81 (m, 3H), 1.73 (br s, 1H), 1.64 - 1.40 (m, 4H), 1.41 (s, 9H),1.32 (d, J = 7.1 Hz, 2H). 13C NMR (100 MHz, CHCl3) δ171.8, 168.8, 163.7, 156.4, 155.4, 136.6, 134.7, 132.0, 129.9 (2C), 129.3,128.8 (2C), 128.5, 128.4 (2C), 128.0 (2C), 127.9, 126.8, 114.6 (2C), 80.1,78.5, 66.5, 60.3, 59.1, 55.6, 54.2, 48.8, 40.4, 34.2, 32.3, 29.1, 28.3, 22.3,21.0, 14.4. MS (ESI) m/z (%) =790.48 (100, [M + Na]+).

Reference： [1]Contini, Alessandro; Lenci, Elena; Trabocchi, Andrea [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 20]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	622-30-0	MDL No. :	MFCD06654467
Formula :	C₇H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LVCDXCQFSONNDO-UHFFFAOYSA-N
M.W :	123.15	Pubchem ID :	2794173
Synonyms :

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.94
TPSA :	32.26 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

[ CAS No. 622-30-0 ]

Quality Control of [ 622-30-0 ]

Related Doc. of [ 622-30-0 ]

Product Details of [ 622-30-0 ]

Calculated chemistry of [ 622-30-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 622-30-0 ]

Application In Synthesis of [ 622-30-0 ]

[ 622-30-0 ] Synthesis Path-Upstream 1~2

[ 622-30-0 ] Synthesis Path-Downstream 1~68

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	1.17
Log Po/w (XLOGP3) :	1.03
Log Po/w (WLOGP) :	1.01
Log Po/w (MLOGP) :	1.42
Log Po/w (SILICOS-IT) :	0.91
Consensus Log Po/w :	1.11

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.61
Solubility :	3.0 mg/ml ; 0.0243 mol/l
Class :	Very soluble
Log S (Ali) :	-1.3
Solubility :	6.21 mg/ml ; 0.0504 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.23
Solubility :	0.72 mg/ml ; 0.00585 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501	UN#:	2923
Hazard Statements:	H301-H318	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling