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

HRID 1891993

Reaktionsgleichung

Reaktionsgleichung von HRID 1891993
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 67159003methyl (2RS,4RS)-2-(3-phenylphenyl)-6-hydroxy-2,4-dimethylcyclohexanecarboxylateAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a2a66f9ce27b48e69bfa8b0416d6db20
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507559B2

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