Name: 1501-04-8|Methyl 4-Benzoylbutyrate|97%
Brand: Ambeed
SKU: A196542
Price: 17.0 USD
Availability: InStock
Rating: 94 (29 reviews)

1
[ 1501-04-8 ]
[ 91132-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; ethanol Erwaermen des Reaktionsprodukts in Chloroform;
	With ammonium hydroxide; ethanol Erwaermen des Reaktionsprodukts in Tetrachlormethan;
	With ammonium hydroxide; ethanol Erwaermen des Reaktionsprodukts in Wasser;

With ammonium hydroxide; ethanol Erwaermen des Reaktionsprodukts in Benzol;

Reference： [1]Allen; Ball [Journal of the American Chemical Society, 1937, vol. 59, p. 686,687]
[2]Allen; Ball [Journal of the American Chemical Society, 1937, vol. 59, p. 686,687]
[3]Allen; Ball [Journal of the American Chemical Society, 1937, vol. 59, p. 686,687]
[4]Allen; Ball [Journal of the American Chemical Society, 1937, vol. 59, p. 686,687]

2
[ 1501-04-8 ]
[ 77287-34-4 ]
[ 41419-25-4 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1944,vol. 64,p. 199
Chem.Abstr.,1951,p. 2862

3
[ 67-56-1 ]
[ 1501-05-9 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With acetyl chloride at 0 - 20℃; for 15h; Inert atmosphere;
97%	With sulfuric acid for 1h;
97%	With sulfuric acid

96%	With acetyl chloride at 0 - 20℃;
95%	With tert.-butylnitrite at 40℃; for 48h;	35 Add compound 1ai (0.5 mmol, 96.2 mg) and methanol containing 40 mol% tert-butyl nitrite to the reaction tube; then react for 48 hours at 40°C in air; after the reaction, add sodium thiosulfate and stir. After quenching, using a rotary evaporator to remove the solvent, adsorbing on silica gel, and finally performing column chromatography with a mixed solvent of ethyl acetate and petroleum ether to obtain the product 3ai with a yield of 95%.
95%	With tert.-butylnitrite at 40℃; for 48h; Green chemistry;
92%	With sulfuric acid at 68℃;
90%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
85%	With sulfuric acid In benzene for 3h; Heating;
85%	With diazomethyl-trimethyl-silane In hexane; dichloromethane at 25℃; for 16h;	1 Weigh 1.9221g benzoylbutyric acid (0.01mol) and place it in a round bottom flask,Add 20mL dichloromethane and 10mL methanol,Stir until completely dissolved;Take 20mL of 2mol/L trimethylsilyldiazomethane in n-hexane solution,Add to the benzoyl butyric acid solution four times,Add 5mL each time, with an interval of 1h twice,Stir at room temperature (25°C) for 16h,Evaporate and concentrate, use n-hexane: ether=1:1 as the mobile phase on a silica gel column,Obtain methyl benzoylbutyrate (1.7531g, yield: 85%),It is a light yellow oil phase, and the liquid chromatogram of the product is shown in Figure 3.It can be seen from Figure 3 that the result of the liquid phase is a single peak,Without other impurity peaks,From this result, it can be considered that the purity of methyl benzoyl butyrate prepared by this method is relatively high.
53%	With toluene-4-sulfonic acid In benzene for 18h; Reflux;
	With hydrogenchloride
	With sulfuric acid
	With hydrogenchloride
	With pyridinium p-toluenesulfonate Yield given;
	With toluene-4-sulfonic acid In chloroform at 61℃;
	With thionyl chloride
	With sulfuric acid
	With sulfuric acid for 2h; Reflux;
4.9 g	With acetyl chloride at 0 - 20℃; for 24h;

Reference： [1]Schlegel, Marcel; Schneider, Christoph [Organic Letters, 2018, vol. 20, # 10, p. 3119 - 3123]
[2]Downham, Robert; Edwards, Paul J.; Entwistle, David A.; Hughes, Andrew B.; Kim, Kun Soo; Ley, Steven V. [Tetrahedron Asymmetry, 1995, vol. 6, # 10, p. 2403 - 2440]
[3]Periasamy, Mariappan; Gurubrahamam, Ramani; Muthukumaragopal, Gopal P. [Tetrahedron Asymmetry, 2013, vol. 24, # 9-10, p. 568 - 574]
[4]Pulipaka, Aravinda B.; Bergmeier, Stephen C. [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1462 - 1467]
[5]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN112552171, 2021, A Location in patent: Paragraph 0057-0058
[6]Cheng, Xionglve; Jiang, Gangzhong; Li, Xingxing; Tao, Suyan; Wan, Xiaobing; Zhao, Yanwei; Zheng, Yonggao [European Journal of Organic Chemistry, 2021, vol. 2021, # 18, p. 2713 - 2718]
[7]Mourelle-Insua, Ángela; Zampieri, Luiz Arthur; Lavandera, Iván; Gotor-Fernández, Vicente [Advanced Synthesis and Catalysis, 2018, vol. 360, # 4, p. 686 - 695]
[8]Shi, Yongjie; Tan, Xuefeng; Gao, Shuang; Zhang, Yao; Wang, Jingxin; Zhang, Xumu; Yin, Qin [Organic Letters, 2020, vol. 22, # 7, p. 2707 - 2713]
[9]Zheng, Liping; Zhou, Qingmei; Deng, Xianyu; Yuan, Min; Yu, Gang; Cao, Yong [Journal of Physical Chemistry B, 2004, vol. 108, # 32, p. 11921 - 11926]
[10]Current Patent Assignee: WUXI UTMOST LIGHT TECHNOLOGY CO LTD - CN111875494, 2020, A Location in patent: Paragraph 0055-0056
[11]Shu, Chunying; Xu, Wei; Slebodnick, Carla; Champion, Hunter; Fu, Wujun; Reid, Jonathan E.; Azurmendi, Hugo; Wang, Chunru; Harich, L Kim; Dorn, Harry C.; Gibson, Harry W. [Organic Letters, 2009, vol. 11, # 8, p. 1753 - 1756]
[12]Allen; Cressman [Journal of the American Chemical Society, 1933, vol. 55, p. 2953,2958] Sugimoto [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, # 4, p. 199][Chem.Abstr., 1951, p. 2862]
[13]Pasto,D.J.; Serve,M.P. [Journal of the American Chemical Society, 1965, vol. 87, p. 1515 - 1521] Taylor, Edward C.; Conley, Richard A.; Katz, Alan H; McKillop, Alexander [Journal of Organic Chemistry, 1984, vol. 49, # 20, p. 3840 - 3841]
[14]Din, Laily Bin; Meth-Cohn, Otto; Walshe, Nigel D. A. [Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 781 - 786]
[15]Pearson, William H.; Walters, Michael A.; Oswell, Kira D. [Journal of the American Chemical Society, 1986, vol. 108, # 10, p. 2769 - 2771]
[16]Hassarajani, S. A.; Dhotare, B.; Chattopadhyay, A.; Mamdapur, V. R. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 1, p. 80 - 81]
[17]Hartung, Jens; Greb, Marco [Tetrahedron Letters, 2003, vol. 44, # 32, p. 6091 - 6093]
[18]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]
[19]Location in patent: scheme or table Starodubtseva; Turova; Antipova; Vinogradov; Sagirova; Malyshev; Struchkova [Russian Chemical Bulletin, 2010, vol. 59, # 7, p. 1463 - 1466]
[20]Jana, Sadhan; Kumar, Sangit; Rathore, Vandana; Verma, Ajay [Synlett, 2019, vol. 30, # 14, p. 1667 - 1672]
[21]Moriyama, Katsuhiko; Kuramochi, Masako; Tsuzuki, Seiji; Fujii, Kozo; Morita, Takeshi [Organic Letters, 2021, vol. 23, # 2, p. 268 - 273]

4
[ 1501-04-8 ]
[ 1501-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; isopentyl nitrite In diethyl ether

Reference： [1]Taylor,E.C.; McKillop,A. [Journal of the American Chemical Society, 1965, vol. 87, p. 1984 - 1990]

5
[ 13735-81-4 ]
[ 292638-85-8 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
	With titanium tetrachloride In dichloromethane at -78℃;

Reference： [1]Narasaka,K. et al. [Bulletin of the Chemical Society of Japan, 1976, vol. 49, p. 779 - 783]

6
[ 67-56-1 ]
[ 80706-73-6 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogen cation In tetrachloromethane Ambient temperature;

Reference： [1]Lechevallier, A.; Huet, F.; Conia, J.M. [Tetrahedron, 1983, vol. 39, # 20, p. 3329 - 3336]
[2]Huet, Francois; Lechevallier, Andre; Conia, Jean-Marie [Chemistry Letters, 1981, p. 1515 - 1518]

7
[ 1501-04-8 ]
[ 1779-49-3 ]
[ 102312-78-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran for 1h; cooling; Stage #2: Methyl 4-benzoylbutanoate In tetrahydrofuran at -78 - 20℃; Further stages.;
66%	Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Inert atmosphere; Stage #2: Methyl 4-benzoylbutanoate In tetrahydrofuran; toluene at -78 - 20℃; for 17h; Inert atmosphere;
43%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 1h; Stage #2: Methyl 4-benzoylbutanoate In tetrahydrofuran at -78 - 20℃; for 18h;

	With potassium <i>tert</i>-butylate In tetrahydrofuran
	Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Inert atmosphere; Stage #2: Methyl 4-benzoylbutanoate In tetrahydrofuran; toluene at -78 - 20℃; for 20h; Inert atmosphere;

Reference： [1]Pulipaka, Aravinda B.; Bergmeier, Stephen C. [Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1462 - 1467]
[2]Murai, Kenichi; Matsushita, Tomoyo; Nakamura, Akira; Fukushima, Shunsuke; Shimura, Masato; Fujioka, Hiromichi [Angewandte Chemie - International Edition, 2010, vol. 49, # 48, p. 9174 - 9177]
[3]Moriyama, Katsuhiko; Kuramochi, Masako; Tsuzuki, Seiji; Fujii, Kozo; Morita, Takeshi [Organic Letters, 2021, vol. 23, # 2, p. 268 - 273]
[4]Pearson, William H.; Walters, Michael A.; Oswell, Kira D. [Journal of the American Chemical Society, 1986, vol. 108, # 10, p. 2769 - 2771]
[5]Jana, Sadhan; Kumar, Sangit; Rathore, Vandana; Verma, Ajay [Synlett, 2019, vol. 30, # 14, p. 1667 - 1672]

8
[ 1501-04-8 ]
[ 142484-33-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bromine In diethyl ether at 20℃; for 1h;	1 Reference Example 1 Reference Example 1 To a solution of methyl 5-oxo-5-phenylpentanoate (16.1 g) in diethyl ether (100 ml) was added bromine (4.01 ml) at room temperature over 30 min. and the mixture was stirred for 30 min.. An aqueous sodium sulfite solution was added to the reaction mixture and the mixture was extracted with diethyl ether.. The diethyl ether layer was washed with saturated brine, dried (MgSO4) and concentrated to give methyl 4-bromo-5-oxo-5-phenylpentanoate (22.1 g, yield 100%) as a pale-yellow oil. NMR(CDCl3)δ: 2.30-2.67(4H, m), 3.70(3H, s), 5.38(1H, dd, J=5.6, 8.2 Hz), 7.44-7.54(2H, m), 7.56-7.66(1H, m), 8.00-8.06(2H, m). Reference Example 2
98%	With bromine

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1394154, 2004, A1 Location in patent: Page 40
[2]Zask, Arie [Journal of Organic Chemistry, 1992, vol. 57, # 16, p. 4558 - 4560]

9
[ 1501-04-8 ]
[ 112022-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	With borane In tetrahydrofuran at 0℃; for 0.416667h; Yield given;

Reference： [1]Corey, E. J.; Bakshi, Raman K.; Shibata, Saizo; Chen Chung-Pin; Singh, Vinod K. [Journal of the American Chemical Society, 1987, vol. 109, # 25, p. 7925 - 7926]

10
[ 76355-55-0 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With chlorosulfonic acid In methanol for 120h;

Reference： [1]Miura, Masahiro; Nojima, Masatomo; Kusabayashi, Shigekazu [Journal of the Chemical Society. Perkin transactions I, 1980, p. 2909 - 2913]

11
[ 1501-26-4 ]
[ 100-58-3 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper(I) bromide; lithium bromide In tetrahydrofuran for 0.5h; Ambient temperature;
87%	With copper(I) bromide; lithium bromide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;

Reference： [1]Babudri, Francesco; Fiandanese, Vito; Marchese, Giuseppe; Punzi, Angela [Tetrahedron, 1996, vol. 52, # 42, p. 13513 - 13520]
[2]Parmar, Dixit; Matsubara, Hiroshi; Price, Kieran; Spain, Malcolm; Procter, David J. [Journal of the American Chemical Society, 2012, vol. 134, # 30, p. 12751 - 12757]

12
[ 1501-04-8 ]
[ 40297-30-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: Methyl 4-benzoylbutanoate With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at -5 - 20℃; for 12.3333h; Inert atmosphere; Stage #2: With sulfuric acid; water In methanol at 20℃; for 3h;	3.1. Typical procedure for Mg-promoted reductive intramolecular coupling of aromatic δ-ketoesters, 2a-g, 7a-c, 9, 14a-f, and -ketoester 3 General procedure: Into a 50-mL three-necked flask were introduced 30 mL of anhydrous N,N-dimethylformamide (DMF) as solvent, 10 equiv mol Mg turning for Grignard reaction, and 2.5 equiv of trimethylsilyl chloride (TMSCl) were added under nitrogen atmosphere, and the solution was stirred at room temperature for 0.5 h. Then the mixture of an aromatic δ-ketoesters, 2a-g, 7a-c, 9, 14a-f, or -ketoester 3 (5.0 mmol) and the additional 2.5 equiv of TMSCl dissolved in 15 mL of anhydrous DMF were added dropwise to the above DMF solution at -5 to 0 °C over 20 min. The reaction mixture was stirred at room temperature for 12 h. After the reaction, the mixture was poured into satd NaHCO3 solution. Organic materials were extracted with three 150-mL portions of ethyl ether. The combined ethereal solution was concentrated under reduced pressure to give the residual oil, which was then treated with 5% sulfuric acid in 50% aqueous methanol at room temperature for 3 h. In the case of the reaction of 14a-f, each of the reaction mixture was found to consist of a complex mixture of several components. Then, the mixture was further treated with 10% aqueous sulfuric acid for another 3 h. The organic components were then extracted with ethyl ether three times, and the combined ethereal solution was dried over anhydrous MgSO4. After removal of MgSO4 by filtration and evaporation of the solvent, isolation by column chromatography gave the corresponding cyclization products in satisfactory yield.
43%	Stage #1: Methyl 4-benzoylbutanoate With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With sulfuric acid In methanol at 20℃; for 1h; Inert atmosphere;
	With Cp₂TiPh; water 1.) Et₂O, PhMe, r.t., 1 h; Yield given. Multistep reaction;

78 % Chromat.

Stage #1: Methyl 4-benzoylbutanoate With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 20℃; Stage #2: With sulfuric acid In methanol at 20℃; for 6h; Further stages.;

Reference： [1]Location in patent: experimental part Miyazaki, Takeshi; Maekawa, Hirofumi; Yonemura, Kazuaki; Yamamoto, Yoshimasa; Yamanaka, Yoshiko; Nishiguchi, Ikuzo [Tetrahedron, 2011, vol. 67, # 8, p. 1598 - 1602]
[2]Schlegel, Marcel; Schneider, Christoph [Organic Letters, 2018, vol. 20, # 10, p. 3119 - 3123]
[3]Yamamoto, Yoshihiko; Matsumi, Daisuke; Itoh, Kenji [Chemical Communications, 1998, # 8, p. 875 - 876]
[4]Maekawa, Hirofumi; Yamamoto, Yoshimasa; Shimada, Hisashi; Yonemura, Kazuaki; Nishiguchi, Ikuzo [Tetrahedron Letters, 2004, vol. 45, # 20, p. 3869 - 3872]

13
[ 1501-04-8 ]
[ 1011-61-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium tetrahydroborate In methanol at 20℃;
87%	With sodium tetrahydroborate In methanol at 20℃; for 24h;
60%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃;

	With aluminum oxide; sodium tetrahydroborate In hexane at 40℃;
	Stage #1: Methyl 4-benzoylbutanoate With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Stage #2: With sodium hydroxide In tetrahydrofuran; water	26.A Step A: l-phenylpentane-l,5-diol. A 2.0 M tetrahydrofuran solution of lithium aluminum hydride (2.80 mL, 5.60 mmol) was added to a tetrahydrofuran solution (10 mL) of methyl 5-oxo-5-phenylpentanoate (500 mg, 2.78 mmol) at 0 0C, The reaction mixture was stirred for one hour and quenched with the sequential addition of water (0.2 mL), 10% sodium hydroxide solution (0.2 mL), and water (0.6 mL). It was concentrated in vacuo to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCI3) δ 1.32-1.42 (m, IH), 1.46-1.55 (m, IH), 1.56-1.64 (m, 2H), 1.70-1.78 (m, IH), 1.78-1.88 (m, IH), 3.63 (t, J= 6.6 Hz, 2H), 4.68 (dd, J= 5.7, 7.8 Hz, IH), 7.25-7.30 (m, IH)5 7.32^7.35 (m, 4H).

Reference： [1]Kim, Juryoung; De Castro, Kathlia A.; Lim, Minkyung; Rhee, Hakjune [Tetrahedron, 2010, vol. 66, # 23, p. 3995 - 4001]
[2]Yu, Jun-Lai; Wang, Hui; Zou, Kai-Feng; Zhang, Jia-Rui; Gao, Xiang; Zhang, Dan-Wei; Li, Zhan-Ting [Tetrahedron, 2013, vol. 69, # 1, p. 310 - 315]
[3]Yoshida, Kiyoshi; Horikoshi, Yoichiro; Eta, Masaaki; Chikazawa, Jun; Ogishima, Masayuki; Fukuda, Yohichi; Sato, Hiroki [Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 21, p. 2967 - 2972]
[4]Kamal, Ahmed; Sandbhor, Mahendra; Shaik, Ahmad Ali [Tetrahedron Asymmetry, 2003, vol. 14, # 11, p. 1575 - 1580]
[5]Current Patent Assignee: MERCK & CO INC - WO2009/94242, 2009, A1 Location in patent: Page/Page column 29

14
[ 17851-98-8 ]
[ 292638-85-8 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tetrabutylammomium bromide In tetrahydrofuran for 12h; Heating;
99%	With tetrabutylammomium bromide In tetrahydrofuran for 12h; Heating;

Reference： [1]Yasuda, Makoto; Ohigashi, Noriyuki; Shibata, Ikuya; Baba, Akio [Journal of Organic Chemistry, 1999, vol. 64, # 7, p. 2180 - 2181]
[2]Yasuda, Makoto; Chiba, Kouji; Ohigashi, Noriyuki; Katoh, Yasuhiro; Baba, Akio [Journal of the American Chemical Society, 2003, vol. 125, # 24, p. 7291 - 7300]

15
[ 1501-04-8 ]
[ 1576-35-8 ]
[ 571170-23-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; sodium methylate
97%	In methanol for 6h; Reflux;
83%	In methanol Heating;

Reference： [1]Kreher, David; Cariou, Michel; Liu, Sheng-Gao; Levillain, Eric; Veciana, Jaume; Rovira, Concepcio; Gorgues, Alain; Hudhomme, Pietrick [Journal of Materials Chemistry, 2002, vol. 12, # 7, p. 2137 - 2159]
[2]Shu, Chunying; Xu, Wei; Slebodnick, Carla; Champion, Hunter; Fu, Wujun; Reid, Jonathan E.; Azurmendi, Hugo; Wang, Chunru; Harich, L Kim; Dorn, Harry C.; Gibson, Harry W. [Organic Letters, 2009, vol. 11, # 8, p. 1753 - 1756]
[3]Zheng, Liping; Zhou, Qingmei; Deng, Xianyu; Yuan, Min; Yu, Gang; Cao, Yong [Journal of Physical Chemistry B, 2004, vol. 108, # 32, p. 11921 - 11926]

16
[ 908094-01-9 ]
[ 825-54-7 ]
[ 1501-04-8 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 493 - 498

17
[ 1501-04-8 ]
C₁₂H₁₅⁽²⁾HO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With Cp₂TiCl₂*Zn; water-d2; 2,4,6-collidine hydrochloride at 20℃; for 48h;

Reference： [1]Barrero, Alejandro F.; Rosales, Antonio; Cuerva, Juan M.; Gansäuer, Andreas; Oltra, J. Enrique [Tetrahedron Letters, 2003, vol. 44, # 5, p. 1079 - 1082]

18
[ 75-77-4 ]
[ 1501-04-8 ]
[ 1198-34-1 ]
[ 603126-57-4 ]
1,2-bis(trimethylsilyloxy)-1-methoxy-2-phenylcyclopentane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 39% 2: 23% 3: 20%	With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 20℃; Electrochemical reaction;
1: 38% 2: 29% 3: 4%	With tetrabutyl-ammonium chloride; triethylamine In tetrahydrofuran at 20℃; Electrochemical reaction;

Reference： [1]Kise, Naoki; Arimoto, Kie; Ueda, Nasuo [Tetrahedron Letters, 2003, vol. 44, # 33, p. 6281 - 6284]
[2]Kise, Naoki; Arimoto, Kie; Ueda, Nasuo [Tetrahedron Letters, 2003, vol. 44, # 33, p. 6281 - 6284]

19
[ 1501-04-8 ]
[ 934520-52-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydroxylamine hydrochloride; sodium acetate In methanol at 50℃;
81%	With hydroxylamine hydrochloride; sodium acetate In methanol; water for 5h; Reflux;
	With hydroxylamine hydrochloride; sodium acetate In methanol

With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 1h; Reflux;

Reference： [1]Savarin, Cecile G.; Grise, Christiane; Murry, Jerry A.; Reamer, Robert A.; Hughes, David L. [Organic Letters, 2007, vol. 9, # 6, p. 981 - 983]
[2]Location in patent: experimental part Starodubtseva; Turova; Antipova; Vinogradov; Sagirova; Malyshev; Struchkova [Russian Chemical Bulletin, 2010, vol. 59, # 7, p. 1463 - 1466]
[3]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]
[4]Das, Braja Gopal; Nallagonda, Rajender; Dey, Dhananjay; Ghorai, Prasanta [Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12601 - 12605]

20
[ 67-56-1 ]
[ 23253-31-8 ]
[ 1501-04-8 ]
[ 1501-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 70% 2: 12%	With methanol; iodine; magnesium at 40℃; for 3h;

Reference： [1]Dai, Peng; Dussault, Patrick H.; Trullinger, Tony K. [Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2851 - 2852]

21
[ 1501-26-4 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With iron(III)-acetylacetonate In tetrahydrofuran at -78℃;

Reference： [1]Scheiper, Bodo; Bonnekessel, Melanie; Krause, Helga; Fuerstner, Alois [Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3943 - 3949]

22
[ 623-43-8 ]
[ 100-52-7 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 3-methylpyridin-2-ylamine; benzoic acid In toluene at 150℃; for 72h;

Reference： [1]Jo, Eun-Ae; Jun, Chul-Ho [European Journal of Organic Chemistry, 2006, # 11, p. 2504 - 2507]

23
[ 3724-55-8 ]
[ 100-52-7 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 3-methylpyridin-2-ylamine; benzoic acid In toluene at 150℃; for 4h;

Reference： [1]Jo, Eun-Ae; Jun, Chul-Ho [European Journal of Organic Chemistry, 2006, # 11, p. 2504 - 2507]

24
[ 1501-04-8 ]
[ 39785-37-0 ]
[ 948018-38-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 4 A molecular sieve In toluene Heating;

Reference： [1]Cheemala, Murthy N.; Knochel, Paul [Organic Letters, 2007, vol. 9, # 16, p. 3089 - 3092]

25
[ 1501-04-8 ]
[ 111836-35-2 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 981 - 983

26
[ 1501-04-8 ]
[ 41419-25-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 686 - 695
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 181 - 185

27
[ 1501-04-8 ]
6-methoxy-2-phenyl-2,3,4,5-tetrahydro-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NH₂OH*HCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

29
[ 1501-04-8 ]
(6R,9aS)-6-Phenyl-octahydro-quinolizin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

30
[ 1501-04-8 ]
(6R,9aS)-6-Phenyl-octahydro-quinolizin-2-one oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

31
[ 1501-04-8 ]
(6R,9aS)-6-Cyclohexyl-octahydro-quinolizin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄ 8: H₂ / PtO₂ / acetic acid

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

32
[ 1501-04-8 ]
(1R,6S,9aR)-2-Oxo-6-phenyl-octahydro-quinolizine-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: NH₂OH*HCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

33
[ 1501-04-8 ]
2-oxo-6-phenyl-3,4,6,7,8,9-hexahydro-2<i>H</i>-quinolizine-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NH₂OH*HCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

34
[ 1501-04-8 ]
N-((2R,6R,9aS)-6-Phenyl-octahydro-quinolizin-2-yl)-benzene-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄ 8: H₂ / Pd/C

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

35
[ 1501-04-8 ]
N-((2S,6R,9aS)-6-Phenyl-octahydro-quinolizin-2-yl)-benzene-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄ 8: H₂ / Pd/C

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

36
[ 1501-04-8 ]
(2-Nitro-phenyl)-((2R,6R,9aS)-6-phenyl-octahydro-quinolizin-2-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

37
[ 1501-04-8 ]
(2-Nitro-phenyl)-((2S,6R,9aS)-6-phenyl-octahydro-quinolizin-2-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

38
[ 1501-04-8 ]
SR 14135 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄ 8: H₂ / Pd/C

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

39
[ 1501-04-8 ]
SR 14136 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: NH₂OHHCl; NaOAc / methanol 2: H₂; CH₃CO₂OH / Pd/C 3: p-TsOH 4: i-Bu₃AlH 5: aq. HCl 6: NH₂OHHCl; NaOAc / methanol 7: LiAlH₄ 8: H₂ / Pd/C

Reference： [1]Jong, Ling; Zaveri, Nurulain; Toll, Lawrence [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 181 - 185]

40
[ 108-55-4 ]
[ 1501-04-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: AlCl₃ / 1.) 4 h, 2.) reflux, 1 h 2: PTS
	Multi-step reaction with 2 steps 1: 66 percent / tetrahydrofuran; diethyl ether / 19 h / Ambient temperature 2: 97 percent / H₂SO₄ / 1 h
	Multi-step reaction with 2 steps 1: 83 percent / AlCl₃ / 12 h / Ambient temperature 2: 97 percent / H₂SO₄ / 1 h

	Multi-step reaction with 3 steps 1: Heating 2: SOCl₂ 3: AlCl₃
	Multi-step reaction with 2 steps 1: aluminum (III) chloride 2: sulfuric acid

Reference： [1]Hassarajani, S. A.; Dhotare, B.; Chattopadhyay, A.; Mamdapur, V. R. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 1, p. 80 - 81]
[2]Downham, Robert; Edwards, Paul J.; Entwistle, David A.; Hughes, Andrew B.; Kim, Kun Soo; Ley, Steven V. [Tetrahedron Asymmetry, 1995, vol. 6, # 10, p. 2403 - 2440]
[3]Downham, Robert; Edwards, Paul J.; Entwistle, David A.; Hughes, Andrew B.; Kim, Kun Soo; Ley, Steven V. [Tetrahedron Asymmetry, 1995, vol. 6, # 10, p. 2403 - 2440]
[4]Taylor,E.C.; McKillop,A. [Journal of the American Chemical Society, 1965, vol. 87, p. 1984 - 1990]
[5]Periasamy, Mariappan; Gurubrahamam, Ramani; Muthukumaragopal, Gopal P. [Tetrahedron Asymmetry, 2013, vol. 24, # 9-10, p. 568 - 574]

41
[ 1501-04-8 ]
[ 127047-12-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: KO-tBu / tetrahydrofuran 2: LAH / diethyl ether