Реакция #10036

ord-9c8bc77dc55d4a88890aa30b737c9dda

Уравнение реакции

O=C(O)[C@@H]1C[C@@H](O)CN1
(2S,4R)-trans-4-hydroxyproline
NC=O
formamide
[H][H]
hydrogen
CN1C[C@H](O)C[C@H]1C(=O)O
title compound
Выход 92.1%
CN1C[C@H](O)C[C@H]1C(=O)O
(2S, 4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylic acid
Выход 92.1%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеAfter removing the palladium on charcoal
  2. 2
    Фильтрацияby filtration
  3. 3
    Другоеthe water of the filtrate was removed by distillation under reduced pressure
  4. 4
    ДругоеThe solid residue thus obtained
  5. 5
    ДругоеThe crystals which precipitated
  6. 6
    Фильтрацияwere collected by filtration

Методика

A suspension of (2S,4R)-trans-4-hydroxyproline (5 g), 37% aqueous formamide solution (4.6 g) and 7.5% palladium on charcoal (53% water content, 3.2 g) in water (15 mL) was stirred at room temperature in an atmosphere of high-pressure hydrogen for 10 hours. After removing the palladium on charcoal by filtration, the water of the filtrate was removed by distillation under reduced pressure. The solid residue thus obtained was suspended and stirred in ethanol (25 mL). The crystals which precipitated were collected by filtration to give the title compound (5.1 g, yield 92%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07091363B2uspto-grants-2006_08