2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:854607-74-2
Molecular Formula:C₂₂H₂₆Cl₂N₄O₆
Molecular Weight:513.378
Hs Code.:

Synonyms:2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 11 articles about 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 676559-42-5
methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

: 854607-74-2
2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Et₃N / CH₂Cl₂

2.1: 6.9 g / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

3.1: H₂; quinoline / Pd/BaSO₄ / ethyl acetate / 0.07 h / 20 °C / 1034.3 Torr

4.1: aq. LiOH / ethanol / 2 h / 20 °C

5.1: 5.0 g / 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium*BF₄; Et₃N / dimethylformamide / 20 °C

6.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

6.2: 78 percent / Me₂S / CH₂Cl₂; methanol / 1.5 h

7.1: 93 percent / NaBH₄; NaBH(OAc)3 / CH₂Cl₂; ethanol / 1 h / 20 °C

8.1: triphenylphosphine; dialkyl azodicarboxylate / toluene / Heating

With quinoline; lithium hydroxide; sodium tetrahydroborate; dialkyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 8.1: Mitsunobu reaction;
DOI:10.1021/jm051283e

Reference yield:

: 847943-34-4
(5R)-ethynylpyrrolidine-1,(2S)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 854607-74-2
2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂; quinoline / Pd/BaSO₄ / ethyl acetate / 0.07 h / 20 °C / 1034.3 Torr

2.1: aq. LiOH / ethanol / 2 h / 20 °C

3.1: 5.0 g / 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium*BF₄; Et₃N / dimethylformamide / 20 °C

4.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

4.2: 78 percent / Me₂S / CH₂Cl₂; methanol / 1.5 h

5.1: 93 percent / NaBH₄; NaBH(OAc)3 / CH₂Cl₂; ethanol / 1 h / 20 °C

6.1: triphenylphosphine; dialkyl azodicarboxylate / toluene / Heating

With quinoline; lithium hydroxide; sodium tetrahydroborate; dialkyl azodicarboxylate; hydrogen; sodium tris(acetoxy)borohydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; triphenylphosphine; Pd-BaSO₄; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 6.1: Mitsunobu reaction;
DOI:10.1021/jm051283e

Reference yield:

: 847943-33-3
(2S,5R)-5-Trimethylsilanylethynyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 854607-74-2
2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 6.9 g / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2.1: H₂; quinoline / Pd/BaSO₄ / ethyl acetate / 0.07 h / 20 °C / 1034.3 Torr

3.1: aq. LiOH / ethanol / 2 h / 20 °C

4.1: 5.0 g / 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium*BF₄; Et₃N / dimethylformamide / 20 °C

5.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

5.2: 78 percent / Me₂S / CH₂Cl₂; methanol / 1.5 h

6.1: 93 percent / NaBH₄; NaBH(OAc)3 / CH₂Cl₂; ethanol / 1 h / 20 °C

7.1: triphenylphosphine; dialkyl azodicarboxylate / toluene / Heating

With quinoline; lithium hydroxide; sodium tetrahydroborate; dialkyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 7.1: Mitsunobu reaction;
DOI:10.1021/jm051283e