N-tert-Butoxycarbonyl-(2R,4S)-4-fluoroproline benzyl ester → (2S,4S)-1-((tert-butoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid

HRID 1244202ノート

反応式

HRID 1244202 の反応式
C([O:8][C:9](=[O:23])[C@H:10]1[CH2:14][C@H:13]([F:15])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C1C=CC=CC=1>[Pd].CO>[C:19]([O:18][C:16]([N:11]1[CH2:12][C@@H:13]([F:15])[CH2:14][C@H:10]1[C:9]([OH:23])=[O:8])=[O:17])([CH3:22])([CH3:20])[CH3:21]

参加物

4

反応物 1

HCID 69621870N-tert-Butoxycarbonyl-(2R,4S)-4-fluoroproline benzyl ester

生成物 1

HCID 2756017(2S,4S)-1-((tert-butoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid収率 87.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 887Methanol溶媒

実験手順

Methanol (95 mL) was carefully added to a mixture of 11 (2.8 g, 8.7 mmol) and palladium on carbon (10% w/w, 1.0 g, 0.94 mmol Pd) under Ar(g). A balloon filled with H2(g) was affixed to the reaction flask, and the mixture was stirred overnight. After 24 h, unreacted starting material remained, so an additional 0.95 g (0.89 mmol Pd) of Pd/C were added and a fresh balloon filled with H2(g) was placed on the flask. After stirring overnight, TLC indicated reaction had gone to completion, and the mixture was filtered through Celite. The filtrate was concentrated to a white solid by rotary evaporation under reduced pressure and dried under vacuum, affording 12 (1.8 g, 7.6 mmol, 87%), which was used without further purification.

後処理

  1. additionA balloon filled with H2(g)
  2. waitAfter 24 h
  3. additiona fresh balloon filled with H2(g)
  4. stirringAfter stirring overnight
  5. customreaction
  6. filtrationthe mixture was filtered through Celite
  7. concentrationThe filtrate was concentrated to a white solid by rotary evaporation under reduced pressure
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-ed80efbdbb084cd7a2a12a21bfa5e318
出典データセット
uspto-grants-2006_10
特許番号
US07122521B2

反応ノート

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