3-Methylbutanal → HCID 70479527, compound

Participants

Reaction Steps

Sodium cyanoborohydride (2.0 g) and 3-methylbutanal (2.8 ml) were added to a solution of Intermediate 2 (2.0 g) in ethanol (30 ml) and the mixture stirred for 18 h. The mixture was diluted with NaHCO3 solution and extracted with ethyl acetate (3×). The extract was washed with water (1×), dried and evaporated to give a foam. This was dissolved in ethyl acetate and extracted with dilute hydrochloric acid (3×) and water (1×). These aqueous extracts were brought to pH 10 by the addition of 0.88 NH3 solution and then extracted with ethyl acetate (3×). This extract was washed with water, dried, filtered and evaporated to give a foam. This was purified by column chromatography eluted with chloroform/methanol (9:1) to give a foam which was crystallised from ethyl acetate to give the title compound (565 mg), m.p. 159°-161°, [α]D +24.2°.

Provenance & Evidence