Sodium borohydride → HCID 22878261, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2-(4'-nitrobenzene)methylcyclohexan-1-one (44) in 5 mL of methanol at 0° C. was added portionwise sodium borohydride, and the reaction mixture was allowed to stir at 0° C. for 1.5 h before quenching with saturated aqueous NH4C1. The methanol was removed under diminished pressure, and the resultant aqueous residue was extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, and concentrated under diminshed pressure. Purification by flash column chromatography (silica gel, hexanes/ethyl acetate, 4:1) gave 10 mg (20%) of the desired alcohol 45, along with 18 mg (36%) of the diastereoisomeric alcohol 46 as colorless oils. Data for alcohol 45:1H NMR (400MHz, CDCl3) δ0.92 (m, 1H), 1.11 (m, 1H), 1.28 (m, 3H), 1.60 (m, 2H), 1.76 (m, 1H), 2.02 (m, 1H, 2-H), 2.51 and 3.59 (d of ABq, 2H, benzylic-CH2), 3.27 (m, 1H, 1-H), 7.34 (d, 2H, Ar--H), 8.15 ppm (d, 2H, Ar--H). [Compound 45 is hereinafter also referred to as COMPOUND "I" or 120154] ##STR10##

Provenance & Evidence