Reaction #1340607

ord-d4911e7d4bac4430ba9aef083d0e662c

Reaction equation

[H][H]
hydrogen
CC(C)(C)OC(=O)N[C@@H]1CN(C(=O)OCc2ccccc2)C[C@@H]1C1CC1
(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine
→
CC(C)(C)OC(=O)N[C@@H]1CNC[C@@H]1C1CC1
title compound
CC(C)(C)OC(=O)N[C@@H]1CNC[C@@H]1C1CC1
(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-cyclopropylpyrrolidine

Reactants

[H][H]
hydrogen
CC(C)(C)OC(=O)N[C@@H]1CN(C(=O)OCc2ccccc2)C[C@@H]1C1CC1
(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine

Reagents

[C].[Pd]
palladium carbon

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationAfter filtration
  2. 2
    Concentrationthe filtrate was concentrated under reduced pressure

Procedure

A 10% palladium carbon catalyst (50 mg) was added to a solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine (408 mg, 1.13 mmol) in ethanol (5 mL), followed by stirring in a hydrogen atmosphere under an ordinary pressure at 45° C. for 12 hours. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (255 mg, quantitative amount). The product was employed, without further purification, in the subsequent step.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08455482B2uspto-grants-2013_06