Sodium borohydride → methyl (2RS,4RS)-2-(3-phenylphenyl)-6-hydroxy-2,4-dimethylcyclohexanecarboxylate

HRID 1891993Notes

Reaction equation

HRID 1891993 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:13]3([CH3:25])[CH2:18][CH:17]([CH3:19])[CH2:16][C:15](=[O:20])[CH:14]3[C:21]([O:23][CH3:24])=[O:22])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2[CH:8]=[C:9]([C:13]3([CH3:25])[CH2:18][CH:17]([CH3:19])[CH2:16][CH:15]([OH:20])[CH:14]3[C:21]([O:23][CH3:24])=[O:22])[CH:10]=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67159605methyl (2RS,4RS)-2-(3-phenylphenyl)-2,4-dimethyl-6-oxocyclohexanecarboxylate

Product 1

HCID 67159003methyl (2RS,4RS)-2-(3-phenylphenyl)-6-hydroxy-2,4-dimethylcyclohexanecarboxylateYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (2RS,4RS)-2-(3-phenylphenyl)-2,4-dimethyl-6-oxocyclohexanecarboxylate (131 mg) in methanol (4 mL) at 0° C. was treated with sodium borohydride (44 mg). The resulting mixture was allowed to warm to rt over 30 min. Once at the prescribed temperature, the mixture was stirred for 2 h, and then was concentrated under vacuum. The resulting residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under vacuum to provide methyl (2RS,4RS)-2-(3-phenylphenyl)-6-hydroxy-2,4-dimethylcyclohexanecarboxylate (93 mg) as a mixture of diastereomers. Mass spectrum m/z 361.34 (M+Na+).

Workup

  1. concentrationwas concentrated under vacuum
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a2a66f9ce27b48e69bfa8b0416d6db20
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

Loading…