Sodium borohydride → tert-Butyl 3-hydroxycyclopentanecarboxylate

HRID 1367495Notes

Reaction equation

HRID 1367495 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 14009988tert-Butyl 3-hydroxycyclopentanecarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-725cfe38759e40028e982469be08d622
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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