Reaction #1340611

ord-44bfbc1a0cf8406ea5ff3dac7cae99f3

Reaction equation

[H][H]
hydrogen
C=CC1CN(C(=O)OCc2ccccc2)C[C@H]1NC(=O)OC(C)(C)C
(3S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine
→
CCC1CNC[C@H]1NC(=O)OC(C)(C)C
title compound
CCC1CNC[C@H]1NC(=O)OC(C)(C)C
(3S)-3-(tert-Butoxycarbonyl)amino-4-ethylpyrrolidine

Reactants

[H][H]
hydrogen
C=CC1CN(C(=O)OCc2ccccc2)C[C@H]1NC(=O)OC(C)(C)C
(3S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine
—
( 4S )-form
—
( 4R )-form

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 (15 mg) was added to a solution of (3S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine [an isomer mixture of (4S)-form:(4R)-form (1:4)] (230 mg, 0.66 mmol) in ethanol (8 mL), followed by stirring in a hydrogen atmosphere under an ordinary pressure at room temperature for 12 hours. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound (an isomer mixture of (4S)-form and (4R)-form (1:4)) as a colorless oily substance (148 mg, 100%).

Source

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