HCID 19775331, compound → HCID 19775326, compound

Participants

Reaction Steps

Lithium aluminium hydride (57 mg) was added to a solution of 2-[N-(4-carbamoylphenethyl)-N-methylamino]-1-diphenylmethoxy-2-methylpropane (170 mg -- see Example 42) in tetrahydrofuran (12 ml) and the mixture was stirred at room temperature for 17 hours, heated under reflux for 2 hours, quenched by the sequential dropwise addition with stirring of a solution of water (57 mg) in tetrahydrofuran (1 ml), 15% aqueous sodium hydroxide solution (57 mg) and water (156 mg), stirred at room temperature for 30 minutes and filtered. The filtrate was evaporated and the residue was partitioned between methylene chloride and 5% aqueous sodium carbonate solution. The organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (17 g) using hexane:ether:diethylamine (90:5:5) as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless oil (86 mg, 52%).

Provenance & Evidence