[ CAS No. 131667-57-7 ]

Name: 131667-57-7|tert-Butyl 3,4-dihydropyridine-1(2H)-carboxylate|98%
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SKU: A640806
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Product Details of [ 131667-57-7 ]

CAS No. :	131667-57-7	MDL No. :	MFCD00798175
Formula :	C₁₀H₁₇NO₂	Boiling Point :	218°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	183.25 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 131667-57-7 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P273-P301+P310-P305+P351+P338	UN#:	2810
Hazard Statements:	H301-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 131667-57-7 ]

Upstream synthesis route of [ 131667-57-7 ]
Downstream synthetic route of [ 131667-57-7 ]

[ 131667-57-7 ] Synthesis Path-Upstream 1~4

1
[ 131667-57-7 ]
[ 98303-20-9 ]

Reference： [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158

2
[ 131667-57-7 ]
[ 161157-50-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3.25 h;	[00263] Step A: A solution of m-CPBA (7.53 g, 32.7 mmol) in DCM (10 mL) was added to a solution of tert-butyl 5,6-dihydropyridine-l(2H)-carboxylate (5.00 g, 27.3 mmol) in DCM (20 mL) at 0⁰C. The reaction was stirred at 0⁰C for 15 minutes and then at room temperature for 3 hours. Saturated sodium sulfite solution (20 mL) and saturated sodium bicarbonate solution (30 mL) was added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo to give tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (5.36 g, 99percent) as oil.

Reference： [1] Patent: WO2009/140320, 2009, A1, . Location in patent: Page/Page column 77

3
[ 131667-57-7 ]
[ 325486-45-1 ]
[ 128372-89-4 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8506 - 8513

4
[ 25015-63-8 ]
[ 171288-01-0 ]
[ 865245-32-5 ]
[ 131667-57-7 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 18, p. 7324 - 7330

[ 131667-57-7 ] Synthesis Path-Downstream 1~26

1
[ 75844-69-8 ]
[ 131667-57-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4069 - 4077
[2]ACS Catalysis,2019,vol. 9,p. 9513 - 9517
[3]Tetrahedron Letters,1990,vol. 31,p. 6385 - 6386
[4]Organic Letters,2013,vol. 15,p. 1918 - 1921

2
[ 86953-81-3 ]
[ 131667-57-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N,N,N,N,N,N-hexamethylphosphoric triamide at 160 - 180℃;
86%	With toluene-4-sulfonic acid In toluene for 0.333333h;
63%	Stage #1: tert-butyl 2-hydroxypiperidine-1-carboxylate With 2,6-dimethylpyridine; trifluoroacetic anhydride In toluene at 0℃; for 7h; Stage #2: for 0.333333h; Heating;

Reference： [1]Dieter, R. Karl; Sharma, Ram R. [Journal of Organic Chemistry, 1996, vol. 61, # 12, p. 4180 - 4184]
[2]Wilkinson; Stehle; Beak [Organic letters, 2000, vol. 2, # 2, p. 155 - 158]
[3]Oliveira, Denilson F.; Miranda, Paulo C. M. L.; Correia, Carlos R. D. [Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6646 - 6652]

3
[ 151978-50-6 ]
[ 131667-57-7 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 7687 - 7690

4
[ 75178-90-4 ]
[ 131667-57-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;
36%	With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 16h;
	Multi-step reaction with 2 steps 1: acetic acid / 0.75 h

Reference： [1]Yu, Chengzhi; Hu, Longqin [Tetrahedron Letters, 2001, vol. 42, # 31, p. 5167 - 5170]
[2]Evans, Paul; Fischer, Pauline; Müller-Bunz, Helge; Morris, Morgan [European Journal of Organic Chemistry, 2020]
[3]Yu, Chengzhi; Hu, Longqin [Tetrahedron Letters, 2001, vol. 42, # 31, p. 5167 - 5170]

5
[ 85908-96-9 ]
[ 131667-57-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With lithium triethylborohydride In tetrahydrofuran; toluene at -70℃; for 0.5h; Stage #2: With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride In tetrahydrofuran; toluene at -70 - 20℃; for 2h;
83%	Stage #1: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With lithium triethylborohydride In tetrahydrofuran; toluene at -70 - -60℃; for 1.66667h; Schlenk technique; Inert atmosphere; Stage #2: With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride In tetrahydrofuran; toluene at -55 - 20℃; for 2.41667h; Schlenk technique; Inert atmosphere;
82%	Stage #1: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With diisobutylaluminium hydride In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene for 0.5h; Dean-Stark; Reflux; Inert atmosphere;

68%	Stage #1: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With lithium triethylborohydride Inert atmosphere; Stage #2: With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride Inert atmosphere;
	Multi-step reaction with 2 steps 1.1: KHMDS / tetrahydrofuran; toluene / 1.5 h / -78 °C 1.2: 90 percent / tetrahydrofuran; toluene / 2 h / -78 - 20 °C 2.1: (dppf)PdCl₂; Et₃N / dioxane / 2 h / 50 °C
	Multi-step reaction with 2 steps 1: 94 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 °C 2: 86 percent / p-TsOH / toluene / 0.33 h
	Multi-step reaction with 2 steps 1.1: 89 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: (CF₃CO)2O; 2,6-lutidine / toluene / 7 h / 0 °C 2.2: 63 percent / 0.33 h / Heating
	Multi-step reaction with 2 steps 1: 90 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C 2: 95 percent / HMPA / 160 - 180 °C
	Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C 1.2: 1 h / -78 °C 2.1: palladium diacetate; triphenylphosphine / 1,2-dimethoxyethane / 0.08 h / 20 °C / Inert atmosphere 2.2: 0.67 h / 85 °C / Inert atmosphere
	Stage #1: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With lithium triethylborohydride In tetrahydrofuran; toluene at -78℃; for 1h; Inert atmosphere; Stage #2: With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride In tetrahydrofuran; toluene at -78 - 20℃; for 3h; Inert atmosphere;
	Stage #1: 2-oxopiperidine-1-carboxylic acid tert-butyl ester With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene at 135℃; for 1h; Dean-Stark; Inert atmosphere;

Reference： [1]Yu, Jurong; Truc, Vu; Riebel, Peter; Hierl, Elizabeth; Mudryk, Boguslaw [Tetrahedron Letters, 2005, vol. 46, # 23, p. 4011 - 4013]
[2]Yu, Jurong; Truc, Vu; Riebel, Peter; Hierl, Elizabeth; Mudryk, Boguslaw; Maywald, Matthias; Pfaltz, Andreas [Organic Syntheses, 2008, vol. 85, p. 64 - 71]
[3]Chen, Cheng; Kattanguru, Pullaiah; Tomashenko, Olesya A.; Karpowicz, Rafał; Siemiaszko, Gabriela; Bhattacharya, Ahanjit; Calasans, Vinícius; Six, Yvan [Organic and Biomolecular Chemistry, 2017, vol. 15, # 25, p. 5364 - 5372]
[4]Artamonov, Olexiy S.; Slobodyanyuk, Evgeniy Y.; Volochnyuk, Dmitriy M.; Komarov, Igor V.; Tolmachev, Andrey A.; Mykhailiuk, Pavel K. [European Journal of Organic Chemistry, 2014, vol. 2014, # 17, p. 3592 - 3599]
[5]Occhiato, Ernesto G.; Lo Galbo, Fabrizio; Guarna, Antonio [Journal of Organic Chemistry, 2005, vol. 70, # 18, p. 7324 - 7330]
[6]Wilkinson; Stehle; Beak [Organic letters, 2000, vol. 2, # 2, p. 155 - 158]
[7]Oliveira, Denilson F.; Miranda, Paulo C. M. L.; Correia, Carlos R. D. [Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6646 - 6652]
[8]Dieter, R. Karl; Sharma, Ram R. [Journal of Organic Chemistry, 1996, vol. 61, # 12, p. 4180 - 4184]
[9]Gigant, Nicolas; Dequirez, Geoffroy; Retailleau, Pascal; Gillaizeau, Isabelle; Dauban, Philippe [Chemistry - A European Journal, 2012, vol. 18, # 1, p. 90 - 94]
[10]Bertho, Sylvain; Dondasse, Ismaël; Retailleau, Pascal; Nicolas, Cyril; Gillaizeau, Isabelle [New Journal of Chemistry, 2020, vol. 44, # 17, p. 7129 - 7141]
[11]Imamoto, Tsuneo; Ito, Hajime; Iwamoto, Hiroaki; Ozawa, Yu; Takenouchi, Yuta [Journal of the American Chemical Society, 2021, vol. 143, # 17, p. 6413 - 6422]

6
[ 131667-57-7 ]
[ 219511-71-4 ]
3a,4,5,6,7,7a-hexahydro-1H-imidazo[4,5-b]pyridin-2-ylamine dihydrochloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 8208 - 8211

7
[ 131667-57-7 ]
[ 134441-93-3 ]

Reference： [1]Organic letters,2000,vol. 2,p. 155 - 158

8
[ 828-27-3 ]
[ 141699-59-4 ]
[ 131667-57-7 ]
[ 287952-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water at 20 - 101℃; Heating / reflux;	2 Production of 4- (4-trifluoromethoxyphenoxy) piperidine 40.74 g of 1-t-butoxycarbonyl-4- mesyloxypiperidine obtained in the above Reference Example 1,14. 43 g of 4-trifluoromethoxyphenol and 4.50 g of tetra-n-butyl ammonium chloride were suspended in 72 ml of water. Next, after adding 33.59 g of potassium carbonate to the suspension, the suspension was subjected to reflux for 8 hours (inner temperature: 101°C). After leaving the suspension at room temperature overnight, 216 ml of n-hexane was added thereto and stirring was conducted for 5 minutes. Thereto was added 72 ml of 10% aqueous sodium hydroxide solution and after stirring, the mixture was separated. After washing with water (72 mlx2), the organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and 39.02 g of a mixture of 1-t-butoxycarbonyl-4- (4- trifluoromethoxyphenoxy) piperidine and 1-t- butoxycarbonyl-3, 4-dehydropiperidine was obtained. From 1H-NMR (CDCl3) analysis, the mixture was regarded to contain 28.48 g of 1-t-butoxycarbonyl-4- (4- trifluoromethoxyphenoxy) piperidine and 10.54 g of 1-t- butoxy-3,4-dehydropiperidine. The above mixture was dissolved in 117 ml of ethyl acetate, and 51 ml of 4N-hydrochloric acid-ethyl acetate solution was added thereto dropwise at room temperature over 10 minutes. After stirring the mixture at the room temperature for an hour, thin layer chromatography analysis revealed that the raw materials were not completely consumed, and so further 51 ml of 4N-hydrochloric acid-ethyl acetate solution was added thereto. The mixture was further stirred at room temperature for 3 hours and left overnight at the room temperature. The reaction solution was cooled with ice and 163 ml of 10% aqueous sodium hydroxide solution was carefully poured thereto. The temperature increased to 23°C due to heat generation. The mixture was separated and the ethyl acetate phase was washed with saturated saline (80 ml) and water (80 ml), and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and 19.45 g of pale yellow solid of 4- (4-trifluoromethoxyphenoxy) piperidine was obtained. H-NMR (300 MHz, CDCl3) bppm : 1.54 (1H, br. s), 1.58-1. 73 (2H, m), 1. 94-2. 06 (2H, m), 2.72 (2H, ddd, J = 12.5 Hz, J = 9.4 Hz, J = 3.1 Hz), 3.14 (2H, ddd, J = 12.5 Hz, J = 4.8 Hz, J = 4.8 Hz), 4.33 (1H, ddd, J = 12.3 Hz, J = 8.4 Hz, J = 4.0 Hz), 6.89 (2H, d, J = 9. 1 Hz), 7.12 (2H, d, J = 9.1 Hz). Reference Data 1-t-butoxycarbonyl-4- (4- trifluoromethoxyphenoxy) piperidine: 1H-NMR (300 MHz, CDC13) 8ppm : 1.47 (9H, s), 1.68-1. 82 (2H, m), 1.82-2. 00 (2H, m), 3.29-3. 40 (2H, m), 3.63-3. 78 (2H, m), 4.39-4. 49 (1H, m), 6.90 (2H, d, J = 8.6 Hz), 7.13 (2H, d, J = 8. 6 Hz). 1-t-butoxycarbonyl-3, 4-dehydropiperidine: 1H-NMR (300 MHz, CDC13) 8ppm : 1.46 (9H, s), 2.13 (2H, br. s), 3.49 (2H, t, J = 5. 7 Hz), 3.88 (2H, br, t, J = 2.5 Hz), 5.58-5. 74 (1H, m), 5.74-5. 91 (1H, m).

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2005/92832, 2005, A1 Location in patent: Page/Page column 44-46

9
[ 131667-57-7 ]
[ 161157-50-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3.25h;	G.A [00263] Step A: A solution of m-CPBA (7.53 g, 32.7 mmol) in DCM (10 mL) was added to a solution of tert-butyl 5,6-dihydropyridine-l(2H)-carboxylate (5.00 g, 27.3 mmol) in DCM (20 mL) at 00C. The reaction was stirred at 00C for 15 minutes and then at room temperature for 3 hours. Saturated sodium sulfite solution (20 mL) and saturated sodium bicarbonate solution (30 mL) was added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo to give tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (5.36 g, 99%) as oil.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2009/140320, 2009, A1 Location in patent: Page/Page column 77

10
[ 129888-60-4 ]
[ 65-71-4 ]
[ 1271239-56-5 ]
[ 131667-57-7 ]
[ 85838-94-4 ]

Yield	Reaction Conditions	Operation in experiment
16%; 28%; 23%	With caesium carbonate; In dimethyl sulfoxide; at 120℃; for 3h;	General procedure: Nucleobase (1.5 mmol) and base (1.5 mmol) were heated at 100 C in dry DMF/DMSO (15 ml). Mesyl derivative (1 mmol) dissolved in dry DMF/DMSO (10 ml) was then added dropwise and the mixture was heated at 120 C for 3 h. The solvent was evaporated and product purified on a silica gel using flash chromatography.

Reference： [1]Tetrahedron,2011,vol. 67,p. 1485 - 1500

11
[ 85908-96-9 ]
[ 131667-57-7 ]
[ 86953-81-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 19% 2: 79%	With Schwartz's reagent In tetrahydrofuran at 20℃; Inert atmosphere;	General Procedure: To a solution of Cp2ZrHCl (see table1) in dry THF (5 mL) under nitrogen, lactam (1 mmol) dissolved in THF was added and the mixture was stirred at room temperature. The reaction mixture was loaded directly into a short plug of silica gel (? 1g), eluted with ethyl acetate and the eluted solvent was concentrated in vacuo. The residue was purified by MPLC.
	With diisobutylaluminium hydride In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;
	With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;

Reference： [1]Piperno, Anna; Carnovale, Caterina; Giofr, Salvatore V.; Iannazzo, Daniela [Tetrahedron Letters, 2011, vol. 52, # 51, p. 6880 - 6882]
[2]Chen, Cheng; Kattanguru, Pullaiah; Tomashenko, Olesya A.; Karpowicz, Rafał; Siemiaszko, Gabriela; Bhattacharya, Ahanjit; Calasans, Vinícius; Six, Yvan [Organic and Biomolecular Chemistry, 2017, vol. 15, # 25, p. 5364 - 5372]
[3]Imamoto, Tsuneo; Ito, Hajime; Iwamoto, Hiroaki; Ozawa, Yu; Takenouchi, Yuta [Journal of the American Chemical Society, 2021, vol. 143, # 17, p. 6413 - 6422]

12
[ 1353455-69-2 ]
[ 131667-57-7 ]
[ 1353455-85-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With silver hexafluoroantimonate; 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride In dichloromethane at 20℃; Inert atmosphere; Molecular sieve;

Reference： [1]Li, Xiao-Xiao; Zhu, Li-Li; Zhou, Wen; Chen, Zili [Organic Letters, 2012, vol. 14, # 2, p. 436 - 439]

13
[ 2495-35-4 ]
[ 131667-57-7 ]
[ 1381963-85-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With oxygen; palladium diacetate; copper(II) acetate monohydrate; acetic acid In N,N-dimethyl acetamide at 70℃; for 2h; stereoselective reaction;
68%	With oxygen; palladium diacetate; copper(II) acetate monohydrate In N,N-dimethyl acetamide; acetic acid at 70℃; stereoselective reaction;	3.1.1. Direct coupling General procedure: To a solution of enamide (0.22 mmol) in a mixtureof dimethylacetamide/acetic acid (1:1, 0.60 mL) wasadded Pd(OAc)2 (10% mol) followed by Cu(OAc)2H2O(0.22 mmol) and alkene (0.44 mmol). A slow O2 bubblingwas injected into the solution. The mixture was heated to70 8C until the disappearance of the starting material. Thereaction was then hydrolyzed by the addition of water. Theaqueous layer was extracted with AcOEt and the combinedorganic extracts were washed with a saturated aqueoussolution of NaHCO3, with brine, dried over MgSO4, filteredand concentrated. The products were purified by flashchromatography with petroleum ether/ethyl acetate toyield the desired products.

Reference： [1]Gigant, Nicolas; Gillaizeau, Isabelle [Organic Letters, 2012, vol. 14, # 13, p. 3304 - 3307]
[2]Gigant, Nicolas; Chausset-Boissarie, Laëtitia; Rey-Rodriguez, Romain; Gillaizeau, Isabelle [Comptes Rendus Chimie, 2013, vol. 16, # 4, p. 358 - 362]

14
[ 1466-76-8 ]
[ 131667-57-7 ]
[ 1421692-56-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With silver (II) carbonate; palladium diacetate; propionic acid; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 24h;

Reference： [1]Gigant, Nicolas; Chausset-Boissarie, Laëtitia; Gillaizeau, Isabelle [Organic Letters, 2013, vol. 15, # 4, p. 816 - 819]

15
[ 570-02-5 ]
[ 131667-57-7 ]
[ 1421692-61-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 816 - 819

16
[ 3278-34-0 ]
[ 35387-59-8 ]
[ 131667-57-7 ]
C₂₂H₃₁NO₆S [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2814 - 2817

17
[ 500-22-1 ]
[ 131667-57-7 ]
[ 94-09-7 ]
ethyl 1-(tert-butoxycarbonyl)-1,2,3,4,4a,5,6,10b-octahydro-5-(3-pyridyl)benzo[h][1,6]naphthyridine-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 3-pyridinecarboxaldehyde; p-aminoethylbenzoate With scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.0833333h; Molecular sieve; Inert atmosphere; Stage #2: tert-butyl 1,2,3,4-tetrahydro-1-pyridinecarboxylate In acetonitrile at 20℃; for 72h; Inert atmosphere; Stage #3: With scandium tris(trifluoromethanesulfonate) In acetonitrile for 24h; Inert atmosphere;	Ethyl 1-benzyl-5-(4-methoxycarbonylphenyl)-1,2,3,4,4a,5,6,10b-octahydro-2-oxobenzo[h][1,6]naphthyridine-9-carboxylate, diastereomeric mixture 6c General procedure: To a stirred solution of p-chlorobenzaldehyde, 4a (1.50 g, 10.7 mmol) and ethyl 4-aminobenzoate, 5 (1.76 g, 10.7 mmol) in anhydrous CH3CN (40 mL), 4 Å molecular sieves and Sc(OTf)3 (1.05 g, 2.13 mmol) were added. The mixture was stirred at room temperature under argon atmosphere for 5 min and then treated with a solution of lactam 3 (2.00 g, 10.7 mmol) in anhydrous CH3CN (20 mL). The resulting suspension was stirred at room temperature under argon atmosphere for 3 days. Then, additional Sc(OTf)3 (0.53 g, 1.07 mmol) was added and the reaction mixture was stirred one more day. The resulting mixture was diluted with sat. aq. NaHCO3 (35 mL) and extracted with EtOAc (3 45 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give a yellow oil (4.89 g), which was purified through column chromatography (35-70 μm silica gel, hexane/EtOAc mixtures, gradient elution). On elution with hexane/EtOAc 30:70 to 0:100, the diastereomeric mixture 6a (3.36 g, 66% yield, 1.4:1 diastereomeric ratio (1H NMR)) was isolated as a white solid.

Reference： [1]Di Pietro, Ornella; Viayna, Elisabet; Vicente-García, Esther; Bartolini, Manuela; Ramón, Rosario; Juárez-Jiménez, Jordi; Clos, M. Victòria; Pérez, Belén; Andrisano, Vincenza; Luque, F. Javier; Lavilla, Rodolfo; Muñoz-Torrero, Diego [European Journal of Medicinal Chemistry, 2014, vol. 73, p. 141 - 152]

18
[ 104-88-1 ]
[ 131667-57-7 ]
[ 94-09-7 ]
ethyl 1-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[h][1,6]naphthyridine-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 4-chlorobenzaldehyde; p-aminoethylbenzoate With scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.0833333h; Molecular sieve; Inert atmosphere; Stage #2: tert-butyl 1,2,3,4-tetrahydro-1-pyridinecarboxylate In acetonitrile at 20℃; for 72h; Inert atmosphere;	1 4.1.1 Ethyl 1-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[h][1,6]naphthyridine-9-carboxylate, diastereomeric mixture 8a To a stirred solution of p-chlorobenzaldehyde, 4a (1.36 g, 9.67 mmol) and ethyl 4-aminobenzoate, (1.60 g, 9.69 mmol) in anhydrous CH3CN (25 mL), 4 Å molecular sieves and Sc(OTf)3 (0.95 g, 1.93 mmol) were added. The mixture was stirred at room temperature under argon atmosphere for 5 min and then treated with a solution of enamine 7 (1.80 mL, 1.78 g, 9.70 mmol) in anhydrous CH3CN (12 mL). The resulting suspension was stirred at room temperature under argon atmosphere for 3 days. Then, the resulting mixture was diluted with sat. aq. NaHCO3 (150 mL) and extracted with EtOAc (3 * 200 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give a solid residue (4.75 g), which was purified by column chromatography (35-70 μm silica gel, hexane/EtOAc mixtures, gradient elution). On elution with hexane/EtOAc 80:20 to 70:30, the diastereomeric mixture 8a (2.86 g, 63% yield, 3:1 diastereomeric ratio (1H NMR)) was isolated as a white solid.

19
[ 74754-99-7 ]
[ 131667-57-7 ]
[ 623-48-3 ]
tert-butyl-2-(cyano(methoxyimino)methyl)-3-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: N-methoxy-1-tosylmethanimidoyl cyanide; tert-butyl 1,2,3,4-tetrahydro-1-pyridinecarboxylate; ethyl iodoacetae In benzene for 0.5h; Inert atmosphere; Stage #2: With bis(tri-n-butyltin) In benzene Inert atmosphere; Heating; Stage #3: With di-tert-butoxydiazene In benzene Inert atmosphere; Heating;	General procedure for the three-componentcarbo-oximation with sulfonyloxime (C) (Table 1).Three-component adducts (11-20) General procedure: In a dry two-neck round-bottom flaskequipped with a condenserand a magnetic stirrerwere successively added oximeC(2 equiv, SeeTable 1), iodoesterA(1 equiv) and the desiredalkenepartner B(4 equiv) in benzene (0.4 M). Argon was bubbleddirectly into the flask for 30 min.(Bu3Sn)2(1.5 equiv) was injected and the flask washeated to 60oC. DTBHN was added after5 min, thenevery 90 min if required (TLC). After totalconsumptionof the starting iodide, the resultingmixture was concentrated in vacuoand purified bysilica gel chromatography (Petroleum ether/EtOAc)to afford the desired product.Tert-butyl-2-(cyano(methoxyimino)methyl)-3-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (11)Compound 11 was obtained according tothe general procedure described above from ethyliodoacetateA (53 mg, 0.25 mmol, 1 equiv), sulfonyloxime C (119 mg, 0.5 mmol, 2 equiv), tert-butyl 3,4-dihydropyridine-1(2H)-carboxylate1(197 mg, 1mmol, 4 equiv), (Bu3Sn)2(0.19 mL,0.38 mmol), andDTBHN (4 mg, 0.04 mmol, 10 mol %) added by 5mol % portion every 1.5 h, in degassed benzene(1.5 mL). Concentration in vacuo, followed bypurification by flash chromatography (silica gel, 90/10 PE / EtOAc) afforded 11(69 mg, 78%) as acolorless oil.Rf= 0.4 (PE/EtOAc90/10). IR (ATR)νmax(cm-1) =2957, 2855, 2711, 1732, 1690, 1513, 1278,939.1H NMR (CDCl3, 300 MHz): δ(ppm) =4.91 (d,1H, J= 6 Hz, CH), 4.18 (q, 2H J= 3 and 6 Hz, CH2),4.02 (s, 3H, CH3), 3.94-3.89 (m, 1H, CH), 3.39-3.34(m, 1H, CH), 2.43-2.34 (m, 2H, CH2), 2.18-2.11 (m,2H, CH2), 1.91-1.77 (m, 2H,CH2), 1.45 (s, 9H, 3CH3),1.38 (appearant t, 3H, J= 6 and 3 Hz, CH3), 1.25-1.19 (m, 1H, CH).13C NMR (CDCl3, 75.5 MHz): δ(ppm) = 174.9 (C=O ester), 156.9 (C=O ester), 138.4(C), 105.5 (CN), 81.0 (C),61.2 (C), 60.6 (C), 60.4(C), 43.3 (C), 37.3 (C), 36.3 (C), 28.4 (C), 26.8 (C),23.3 (C), 14.7 (C).HRMS (ESI): [M+H]+C17H28N3O5calcd. 354.1993, found 354.19330.

Reference： [1]Mohammed, Shireen; K, Maher; Halid [Oriental Journal of Chemistry, 2015, vol. 31, # 3, p. 1319 - 1326]

20
[ 131667-57-7 ]
Umemoto's reagent [ No CAS ]
C₁₁H₁₆F₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With dipotassium hydrogenphosphate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Irradiation;	2 Experimental General procedure: General procedure for the synthesis of compound 3 is: a10 mL round bottom flask was equipped with a rubber septum and magnetic stir bar. The flask was charged with enamide1 (0.2 mmol, 1.0 equiv.), Umemoto’s reagent 2 (0.3mmol, 1.5 equiv.) and K2HPO4 (0.3mmol, 1.5 equiv.). The flask was evacuated and backfilled with nitrogen for 3 times. Dimethylformamide (DMF, 2.0 mL, 0.1 mol/L) was added with a syringe under nitrogen. The mixture was then irradiated using white LED strips at room temperaturefor 24 h. After the reaction completed (as judged by TLC analysis), the mixture was poured into a separatory funnel containing 20 mL of H2O and 20 mL of Et2O. The layers were separated and the aqueous layer was extracted with Et2O (2×20 mL). The combined organic layers were driedover Na2SO4 and concentrated under reduced pressure afterfiltration. The crude product was purified by flash chromatography on silica gel to afford the desired product 3.

Reference： [1]Wang, Hao; Cheng, Yuanzheng; Yu, Shouyun [Science China Chemistry, 2016, vol. 59, # 2, p. 195 - 198]

21
[ 3278-34-0 ]
[ 120097-60-1 ]
[ 131667-57-7 ]
C₂₂H₃₅NO₈ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 2439 - 2447

22
[ 131667-57-7 ]
[ 325486-45-1 ]
[ 128372-89-4 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8506 - 8513

23
[ 119-61-9 ]
[ 131667-57-7 ]
tert-butyl 4-(hydroxydiphenylmethyl)-3,4-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; potassium carbonate; triisopropylsilanethiol In N,N-dimethyl acetamide at 20℃; for 24h; Inert atmosphere; Glovebox; Irradiation;
58%	With tris[2-phenylpyridinato-C²,N]iridium(III); potassium thioacetate In acetone at 30℃; for 24h; Inert atmosphere; Irradiation;

Reference： [1]Yip, Benjamin Rui Peng; Pal, Kumar Bhaskar; Lin, Junjie Desmond; Xu, Yuan; Das, Mrinmoy; Lee, Jiande; Liu, Xue-Wei [Chemical Communications, 2021, vol. 57, # 82, p. 10783 - 10786]
[2]Vu, Minh Duy; Das, Mrinmoy; Guo, Aoxin; Ang, Zi-En; Dokić, Miloš; Soo, Han Sen; Liu, Xue-Wei [ACS Catalysis, 2019, vol. 9, # 10, p. 9009 - 9014]

24
[ 131667-57-7 ]
[ 264881-99-4 ]
2-(tert-butyl) 7-methyl (1R,6R,7S)-7-(4-bromophenyl)-2-azabicyclo[4.1.0]heptane-2,7-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) In pentane at 23℃; for 2.5h; Inert atmosphere; enantioselective reaction;

Reference： [1]Babl, Tobias; Davies, Huw M. L.; Liu, Wenbin; Röther, Alexander; Reiser, Oliver [Chemistry - A European Journal, 2019]

25
[ 22979-35-7 ]
[ 131667-57-7 ]
2-(tert-butyl) 7-methyl (1R,6R,7S)-7-phenyl-2-azabicyclo[4.1.0]heptane-2,7-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) In pentane at 0℃; for 2.5h; Inert atmosphere; enantioselective reaction;

Reference： [1]Babl, Tobias; Davies, Huw M. L.; Liu, Wenbin; Röther, Alexander; Reiser, Oliver [Chemistry - A European Journal, 2019]

26
[ 131667-57-7 ]
[ 219564-85-9 ]
2-(tert-butyl) 7-(2,2,2-trichloroethyl) (1R,6R,7S)-7-(4-(trifluoromethyl)phenyl)-2-azabicyclo[4.1.0]heptane-2,7-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) In pentane at 0℃; for 2.5h; Inert atmosphere; enantioselective reaction;

Reference： [1]Babl, Tobias; Davies, Huw M. L.; Liu, Wenbin; Röther, Alexander; Reiser, Oliver [Chemistry - A European Journal, 2019]

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{[ 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 -

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[ CAS No. 131667-57-7 ]

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[ 131667-57-7 ] Synthesis Path-Upstream 1~4

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Pyridines

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