Sodium borohydride → tert-Butyl 3-hydroxycyclopentanecarboxylate

HRID 1367495ノート

反応式

HRID 1367495 の反応式
[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylate

生成物 1

HCID 14009988tert-Butyl 3-hydroxycyclopentanecarboxylate収率 67%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
2.5 °C

実験手順

To a cold (ice bath) solution of Rac-3-Oxo-cyclopentanecarboxylic acid tert-butyl ester (1.43 g) in methanol (9 mL) was added sodium borohydride (0.293 g). The mixture was stirred 25 min at 0-5° C. then concentrated in vacuo. Ethyl acetate was added to the residue and the mixture was washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant to afford the title compound (0.963 g, 67%) as colorless oil. MS (EI): 187.1 (M+H)+.

後処理

  1. concentrationthen concentrated in vacuo
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant

出典と根拠

ORDレコード
ord-725cfe38759e40028e982469be08d622
出典データセット
uspto-grants-2011_02
特許番号
US07893099B2

反応ノート

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