Ethanol → (4-Dimethylamino-4-phenylcyclohexyl)methanol

HRID 1767106Notes

Reaction equation

HRID 1767106 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1.[BH4-].[Na+].C(O)C>[OH-].[Na+].C(O)C.O.O>[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 104439064-Dimethylamino-4-phenylcyclohexanecarbaldehyde

Product 1

HCID 21113403(4-Dimethylamino-4-phenylcyclohexyl)methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 19096565Water ethanolSolvent

Procedure

4-Dimethylamino-4-phenylcyclohexanecarbaldehyde (2.35 g, 10.2 mmol) was stirred in a mixture of 1 M NaOH (10.2 ml) and ethanol/water (2:1, 60 ml) for 30 min at RT under argon as inert gas. A solution of sodium borohydride (769 mg, 20.3 mmol) in water (40 ml) was then added dropwise at RT over 60 min and the mixture was stirred for 2 h. For the work-up, the ethanol was driven off under vacuum and the aqueous residue was extracted with EE (6×20 ml). The combined extracts were washed with saturated NaCl solution (2×20 ml), dried and concentrated. The resulting residue (2.2 g of brown oil) was a mixture of the two diastereoisomers of (4-dimethylamino-4-phenylcyclohexyl)methanol.

Workup

  1. extractionthe aqueous residue was extracted with EE (6×20 ml)
  2. washThe combined extracts were washed with saturated NaCl solution (2×20 ml)
  3. customdried
  4. concentrationconcentrated
  5. additiona mixture of the two diastereoisomers of (4-dimethylamino-4-phenylcyclohexyl)methanol

Sources & evidence

ORD record
ord-d127e507daf64aa5a0d142d2b13cd775
Source dataset
uspto-grants-2007_06
Patent number
US07232847B2

Reaction notes

Loading…