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

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Reaction Steps

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.

Provenance & Evidence