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

HRID 1244202노트

반응식

HRID 1244202 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ed80efbdbb084cd7a2a12a21bfa5e318
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122521B2

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