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

HRID 928087ノート

反応式

HRID 928087 の反応式
[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

参加物

3

反応物 1

HCID 71006894tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-032800e5576d47eb98a4fadfff12b8af
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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