Borane;tetrahydrofuran → Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-(R)-hydroxy-propyl)benzoate

Participants

Reaction Steps

At -20° C., (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo(1,2-c)(1,3,2)oxazaborole (J. Am. Chem. Soc., 104, 5551-5553 (1987), 3.82 g, 0.014 mol) was added to a solution of the ketone of Step 2 in THF (556 mL). To this mixture, 1.0M BH3.THF (111 mL) was slowly added within 10 min. After 15 min, the reaction was quenched with 2M HCl (250 mL). After extraction with EtOAc, the organic phase was washed with 25% aq NH4OAc followed by saturated NaCl. The solvent was removed at reduced pressure to afford an oil which was purified by flash chromatography (20% EtOAc in hexane) to give 70 g (95%) of the title compound.

Provenance & Evidence