tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate → tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate

HRID 928087노트

반응식

HRID 928087 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[CH:6][CH:7]=1>[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 71006894tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate2회

생성물 1

HCID 71006947tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate수율 43.1%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A solution of tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate (Intermediate 235, 1.26 g) in IMS (70 mL) was carefully added to 20% palladium on carbon (0.6 g) under a carbon dioxide atmosphere. The mixture was degassed under vacuum and placed under an atmosphere of hydrogen. This was repeated three times then the mixture was stirred under an atmosphere of hydrogen for 18 hours. The mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of DCM and pentane with a gradient of 0-100% to give tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate (0.55 g) as an oil.

후처리

  1. customThe mixture was degassed under vacuum
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a mixture of DCM and pentane with a gradient of 0-100%

출처 및 근거

ORD 기록
ord-032800e5576d47eb98a4fadfff12b8af
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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