Diisopropylamine → HCID 178455317, compound

Participants

Reaction Conditions

Reaction Steps

A 2.5 M n-butyllithium solution in hexane (0.85 ml, 2.07 mmol) was added to a solution of diisopropylamine (0.23 ml, 2.21 mmol) at −78° C. under an argon stream. The mixture was brought to 0° C., was stirred for 30 min, and was again cooled to −78° C. A solution of benzyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)acetate (500 mg, 1.37 mmol) in anhydrous THF (5.0 ml) was added dropwise at −78° C., and the mixture was stirred for additional one hr. A solution of benzyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-oxoacetate (467 mg, 1.25 mmol) in anhydrous THF (5.0 ml) cooled to −78° C. was added to the resultant enolate solution through a cannula over 10 min. The mixture was stirred at −78° C. for one hr, and the mixture was quenched with acetic acid, was adjusted to pH 4, and was brought to room temperature. The reaction solvent was removed by distillation under reduced pressure, and the residue was diluted with ethyl acetate, and the diluted solution was washed with water and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as a colorless solid (500 mg, yield 50%).

Provenance & Evidence