Sodium borohydride → 4-Hydroxy-cyclopentane-1,2-dicarboxylic acid, dimethyl ester

HRID 1429130Notes

Reaction equation

HRID 1429130 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([C@@H:7]1[CH2:11][C:10](=[O:12])[CH2:9][C@@H:8]1[C:13]([O:15][CH3:16])=[O:14])=[O:6]>CO>[CH3:16][O:15][C:13]([CH:8]1[CH2:9][CH:10]([OH:12])[CH2:11][CH:7]1[C:5]([O:4][CH3:3])=[O:6])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 108996331,2-dimethyl (1R,2S)-4-oxocyclopentane-1,2-dicarboxylate

Product 1

HCID 5601004-Hydroxy-cyclopentane-1,2-dicarboxylic acid, dimethyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.11 g, 0.029 mol) was added to a stirred solution of (1R,2S)-4-oxo-cyclopentane1,2-dicarboxylic acid dimethyl ester (4.88 g, 0.0244 mol) in methanol (300 mL) at 0° C. After 1 h the reaction was quenched with 90 ml brine, concentrated and extracted with ethyl acetate. The organic phases were pooled, dried, filtered and concentrated. The crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1) which gave the title compound (3.73 g, 76%) as a yellow oil.

Workup

  1. customAfter 1 h the reaction was quenched with 90 ml brine
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1) which

Sources & evidence

ORD record
ord-0d4f0fafca1e40148c7432a39726dc7a
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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