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

Participants

Reaction Conditions

Reaction Steps

To compound 3B (0.519 g, 1.39 mmol) in THF (10 mL) at −78° C. was added a 1 M solution of Super-Hydride® in THF (9.73 mL, 9.73 mmol). The cold bath was removed and the reaction was stirred for 2.5 days. The reaction was cooled to −78° C., additional 1 M Super-Hydride® in THF (4.00 mL, 4.00 mmol) was added, and reaction was stirred overnight at rt. The reaction was poured into a 1-L Erlenmeyer flask and was carefully quenched with ice while stirring and then diluted with EtOAc. The layers were separated and the organic layer washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine, dried (MgSO4), filtered and concentrated. The residue was purified via flash chromatography eluting with 20-50% EtOAc/hexane to obtain compound 3C (117 mg) as a clear oil.

Provenance & Evidence