Water → Tert-butyl (2S)-2-[(3-fluoro-4-methylphenyl)(hydroxy)methyl]pyrrolidine-1-carboxylate

HRID 1920778ノート

反応式

HRID 1920778 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:6].[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH:19]=[CH:20][C:21]=1[CH3:22]

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58580634tert-butyl (2S)-2-(3-fluoro-4-methylbenzoyl)pyrrolidine-1-carboxylate

生成物 1

HCID 58580880Tert-butyl (2S)-2-[(3-fluoro-4-methylphenyl)(hydroxy)methyl]pyrrolidine-1-carboxylate収率 96%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of tert-butyl (2S)-2-(3-fluoro-4-methylbenzoyl)pyrrolidine-1-carboxylate (1.35 g, 4.38 mmol), which had been obtained in Example 1 (1a), in methanol (5 mL), sodium borohydride (0.20 g, 5.23 mmol) was added under ice cooling, and stirred at room temperature for 0.5 hours. Water (20 mL) was added to the reaction solution, which was then extracted with ethyl acetate (20 mL×3). After that, the organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound as an orange oily substance (1.30 g, yield 96%).

後処理

  1. extractionwas then extracted with ethyl acetate (20 mL×3)
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-8828d568a4d0493d8ed254fbd5d9bbc7
出典データセット
uspto-grants-2012_05
特許番号
US08173631B2

反応ノート

読み込み中…