Hydrochloric Acid → HCID 19099237, compound

Participants

Reaction Steps

To a stirred solution of 1-(N-allyloxycarbonyl-N-methylamino)-2-(N-allyloxycarbonyl-N-methylaminomethyl)-3-(t-butyldimethylsilyloxy)butane (123 g) in ethyl acetate (1.2 l) was added 6N-aqueous hydrochloric acid (240 ml) at ambient temperature. After stirring at the same temperature for 2.5 hours, to the mixture was added water (1 l) and the organic layer was separated. The organic layer was washed successively with 1N-aqueous sodium hydroxide (1 l), saturated aqueous ammonium chloride (500 ml), and brine (500 ml). After the solution was dried over magnesium sulfate, removal of the solvents gave a residue. The residue was chromatographed on silica gel (1 l) eluting with a mixture of n-hexane and ethyl acetate (95:5-40:60, V/V) to give 1-(N-allyloxycarbonyl-N-methylamino)-2-(N-allyloxycarbonyl-N-methylaminomethyl)-3-hydroxybutan-3-ol (83.18 g).

Provenance & Evidence