Lithiumtriethylborohydride → 1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

Participants

Reaction Steps

To a solution of compound 4A (4.30 g, 12.0 mmol) in THF (75 mL) at −78° C. under nitrogen was added dropwise a solution of 1.0 M lithium triethylborohydride in tetrahydrofuran (60.0 mL, 60.0 mmol). The reaction was allowed to warm to rt and was stirred for 4 h. The reaction was then quenched by pouring over ice (150 g) and stirring for 30 min. The product was extracted into EtOAc and was washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Purification via flash chromatography (silica gel, 0-15% EtOAc in hexane) provided compound 5A (3.30 g).

Provenance & Evidence