Реакция #1340602

ord-7cc8b3c84f7140e384721feb8d44f9e7

Уравнение реакции

CCC[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1NC(=O)OC(C)(C)C
(3S,4S) -1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-propylpyrrolidine
[H][H]
hydrogen
CCC[C@H]1CNC[C@H]1NC(=O)OC(C)(C)C
title compound
CCC[C@H]1CNC[C@H]1NC(=O)OC(C)(C)C
(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-propylpyrrolidine

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеInsoluble matter was removed through filtration by use of Celite
  2. 2
    Другоеethanol was removed under reduced pressure
  3. 3
    workup.DISSOLUTIONThe residue was dissolved in diethyl ether (200 mL)
  4. 4
    Промывкаthe solution was washed by a 1 mol/L aqueous sodium hydroxide solution (100 mL)
  5. 5
    Сушкаby drying over anhydrous sodium sulfate
  6. 6
    ФильтрацияAfter filtration
  7. 7
    Концентрированиеthe filtrate was concentrated under reduced pressure

Методика

A mixture of (3S,4S) -1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-propylpyrrolidine (4.02 g, 11.09 mmol) and a 10% palladium carbon catalyst (1.0 g) in ethanol (100 mL) was stirred hard for 20 hours under an ordinary pressure in a hydrogen atmosphere. Insoluble matter was removed through filtration by use of Celite, and then ethanol was removed under reduced pressure. The residue was dissolved in diethyl ether (200 mL), and the solution was washed by a 1 mol/L aqueous sodium hydroxide solution (100 mL), followed by drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (2.34 g, 92.4%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08455482B2uspto-grants-2013_06