(3S)-(+)-1-Benzyl-3-aminopyrrolidine → (2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate
Reaction equation
[C:1](=O)([O:12][C@@H:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])[O:2]C1C=CC([N+]([O-])=O)=CC=1.[CH2:20]([N:27]1[CH2:31][CH2:30][C@H:29]([NH2:32])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[CH2:20]([N:27]1[CH2:31][CH2:30][C@H:29]([NH:32][C:1](=[O:2])[O:12][C@@H:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
4
Procedure
To a solution of 4-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate (2.20 g) in CHCl3 (30 ml) was added (3S)-1-benzylpyrrolidin-3-amine (1.39 g) at room temperature. The resulting mixture was refluxed for 2 hours and then cooled to room temperature. The mixture was purified with silica gel column chromatography (eluent:hexane/EtOAc=1/0˜0/1) to give (2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate as a pale yellow oil.