Water → (2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid amide

HRID 890255Notes

Reaction equation

HRID 890255 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:6]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=O.O.[OH-].[NH4+:29]>CO>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]2[N:6]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:5]([C:3]([NH2:29])=[O:2])[CH2:9][CH2:8]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 69596768(2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 22250472(2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (1.3 g, 3.44 mmol) in MeOH (75 ml) and ammonium hydroxide solution (50 ml, 25%) was stirred at room temperature for 72 h. The volume of the solution was reduced to 50 ml and water (150 ml) was added. The title compound precipitated as a white solid (0.95 g, yield 76%), m.p. 137° C. and MS: m/e=363.1 (M+H+).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-b792ecc998084e1ca658ec8d83be6b4b
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

Loading…