Lithiumtriethylborohydride → (2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethyl-2-methylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Participants

Reaction Steps

To a solution of 4B (206 mg, 0.550 nmol) in THF (5 mL) at −78° C. under nitrogen was added dropwise 1.0 M lithium triethylborohydride in tetrahydrofuran (3.00 mL, 3.00 mmol). The reaction was allowed to warm to rt and was stirred for 4 h. The reaction was quenched by pouring over ice (50 g) and stirring for 30 min. The product was extracted into EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. Purification via silica gel chromatography (0-15% EtOAc in hexane) provided the title compound (131 mg).

Provenance & Evidence