Potassium Hydroxide → Ammonia

Participants

Reaction Steps

A suspension of the product of example 97 (70 mg, 0.13 mmol) and powdered potassium hydroxide (144 mg, 2.57 mmol) in 3-methyl-4-pentanol (4 mL) was heated under reflux for 36 hours. The reaction mixture was allowed to cool to room temperature and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate (30 mL) and water (20 mL). The organic layer was separated, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 95:5:0.5 to 90:10:1. Appropriate fractions were concentrated in vacuo and the residue further purified by chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 98:2:0.2 to 95:5:0.5, to afford the title compound as a gum in 21% yield.

Provenance & Evidence