Sodium Hydroxide → {4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexyl}-methanol

HRID 557521Notes

Reaction equation

HRID 557521 reaction equation
[CH3:1][N:2]([CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7][CH2:6]1)[CH3:3].[OH-].[Na+].[BH4-].[Na+]>C(O)C.O>[CH3:3][N:2]([CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 866278884-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexane-carbaldehyde

Product 1

HCID 24740060{4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexyl}-methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

The aldehyde 34 (7.11 g, 27 mmol) was dissolved, under argon, in ethanol (120 ml), water (60 ml) and 1N NaOH (27 ml, 27 mmol) and stirred for 30 minutes at RT. A solution of NaBH4 (2.04 g, 54 mmol) in water (200 ml) was then slowly added dropwise and the mixture was stirred overnight. Ethanol was removed in vacuo, the aqueous residue was extracted three times with ethyl acetate (100 ml each time), and the organic phase was washed with water (100 ml) and saturated NaCl solution (100 ml), dried (Na2SO4) and concentrated in vacuo.

Workup

  1. customEthanol was removed in vacuo
  2. extractionthe aqueous residue was extracted three times with ethyl acetate (100 ml each time)
  3. washthe organic phase was washed with water (100 ml) and saturated NaCl solution (100 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2161adc640c40fb8c0cd8e988e6dcc1
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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