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

HRID 1891993

반응식

HRID 1891993 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-a2a66f9ce27b48e69bfa8b0416d6db20
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507559B2

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