Sodium borohydride → 4-(Benzylamino)-1,1-dimethoxybutan-2-ol

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Reaction Steps

To a solution of (E)-4-(benzylamino)-1,1-dimethoxybut-3-en-2-one (4.71 g, 20 mmol) in a mixture of 2-Propanol (60 ml) and Water (4.80 ml) was added sodium borohydride (3.03 g, 80 mmol) in portions at 20-25° C., the mixture was stirred overnight. Quenched with 5N HCl to pH 7 (approx 10 ml), pH adjusted to 8-9 with 5N NaOH, diluted with MTBE (100 ml) and brine (50 ml). Organic phase was dried (MgSO4), evaporated, separated on a column with ethyl acetate-MeOH mixture 4:1, fractions collected to give 4-(benzylamino)-1,1-dimethoxybutan-2-ol (3.55 g, 14.83 mmol, 74.2% yield), colorless oil.

Provenance & Evidence