(3S)-(+)-1-Benzyl-3-aminopyrrolidine → (2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate

HRID 452857Notes

Reaction equation

HRID 452857 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]=1

Participants

4

Reactant 2

HCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 687562104-nitrophenyl (2S)-1,1,1-trifluoropropan-2-yl carbonate

Product 1

HCID 68029098(2S)-1,1,1-trifluoropropan-2-yl [(3S)-1-benzylpyrrolidin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. customThe mixture was purified with silica gel column chromatography (eluent:hexane/EtOAc=1/0˜0/1)

Sources & evidence

ORD record
ord-fb99d7c7f2aa482583af9d293dacc413
Source dataset
uspto-grants-2013_07
Patent number
US08492397B2

Reaction notes

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