tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate → 2-(S)-(3-dimethylaminomethylene-thioureidomethyl)-pyrrolidine-1-carboxylic acid 1,1-dimethylethyl ester
Reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])[CH3:3].C(OC(N1CCC(CN[C:30]([N:32]=[CH:33][N:34]([CH3:36])[CH3:35])=[S:31])CC1)=O)(C)(C)C>>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:30]([N:32]=[CH:33][N:34]([CH3:36])[CH3:35])=[S:31])=[O:7])([CH3:1])[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
2-(S)-(3-dimethylaminomethylene-thioureidomethyl)-pyrrolidine-1-carboxylic acid 1,1-dimethylethyl ester was prepared from (S)-2-(aminomethyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester according to the procedure described in Example A (4-(3-dimethylaminomethylene -thioureidomethyl)-piperidine-1-carboxylic acid tert-butyl ester). Purified by column chromatography on silica gel (2:1 to 3:1 ethyl acetate/hexane eluant). Yellow solid. MS: 315.4 (M+H)+