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

HRID 1891993

反応式

HRID 1891993 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a2a66f9ce27b48e69bfa8b0416d6db20
出典データセット
uspto-grants-2013_08
特許番号
US08507559B2

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