(2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid amide → (2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbonitrile
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([C:23]([NH2:25])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[P+]=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:15])=[O:14])[CH:11]([C:23]#[N:25])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
3
Procedure
A stirred mixture of (2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid amide (1.15 g, 3.17 mmol) and phosphorus oxide chloride (8 ml) was heated for 5 min under reflux conditions. Aqueous work-up and crystallization from ethyl acetate/hexane yielded the title compound as a light brown solid (0.9 g, yield 82%), m.p. 128° C. and MS: m/e=344 (M+).