HCID 14555476, compound → (S)-1-Cbz-3-Aminopyrrolidine

HRID 2073175Notes

Reaction equation

HRID 2073175 reaction equation
[N:1]([C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5]1)=[N+]=[N-].[H][H]>CO.[Ni]>[NH2:1][C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5]1

Participants

5

Reactant 2

HCID 14555476HCID 14555476, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1519355(S)-1-Cbz-3-AminopyrrolidineYield 99.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 14.7 g (60 mmol) of (S)-3-azido-1-pyrrolidinecarboxylic acid, phenylmethyl ester in 200 ml of methanol was treated with 1.0 g of Raney-nickel and shaken in a hydrogen atmosphere at pressures of 49.5-51 psi and temperatures of 25.3-29.5° for nine hours. The catalyst was removed by filtration and the solvent was removed in vacuo to give 13.2 g of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8b2f28a8ca7546a98cfefefd9d3c87dd
Source dataset
uspto-grants-1990_04
Patent number
US04916141

Reaction notes

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