Borane → HCID 86759700, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-Methyl-CBS-oxazaborolidine (1M in toluene, 0.84 ml, 0.836 mmol) was added to anhydrous tetrahydrofuran (50 ml) and the solution cooled to 0° C. Borane:tetrahydrofuran complex (1M, 5.02 ml, 5.02 mmol) was then added dropwise, keeping the temperature at 0° C. The mixture was stirred for 15 minutes then added the product of step (a) (2.0 g, 8.36 mmol) as a solution in tetrahydrofuran (50 ml), dropwise over 1 h keeping the temperature at 0° C. Stirred overnight whilst allowing to warm to room temperature. The reaction was quenched with methanol (5 ml) and stirred for a half hour. The solvent was removed in vacuo and another aliquot of methanol (20 ml) added. The solvent was removed in vacuo and the residue chromatographed on flash silica, eluting with hexane:ethyl acetate (1:1), to give the title compound as a colourless oil (1.685 g, 84%).

Provenance & Evidence