تفاعل #10036

ord-9c8bc77dc55d4a88890aa30b737c9dda

معادلة التفاعل

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
المردود 92.1%
CN1C[C@H](O)C[C@H]1C(=O)O
(2S, 4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylic acid
المردود 92.1%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىAfter removing the palladium on charcoal
  2. 2
    ترشيحby filtration
  3. 3
    أخرىthe water of the filtrate was removed by distillation under reduced pressure
  4. 4
    أخرىThe solid residue thus obtained
  5. 5
    أخرىThe crystals which precipitated
  6. 6
    ترشيحwere collected by filtration

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07091363B2uspto-grants-2006_08