Reacción #1340611

ord-44bfbc1a0cf8406ea5ff3dac7cae99f3

Ecuación de reacción

[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

Reactantes

[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

Reactivos

[C].[Pd]
palladium carbon

Disolventes

CCO
ethanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónAfter filtration
  2. 2
    Concentraciónthe filtrate was concentrated under reduced pressure

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08455482B2uspto-grants-2013_06