(2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate → HCID 10979991, compound

Participants

Reaction Steps

A solution of (2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate (5.34 g, 13.0 mmol) in THF (30 mL) was cooled to about 0° C. and a solution of lithium triethylborohydride (1M in THF, 52 mL) was added dropwise. The ice-bath was removed and the reaction mixture was stirred at ambient temperature for about 2 hours. The reaction mixture was cooled to about 0° C. and additional lithium triethylborohydride solution (10 mL) was added. The reaction mixture was stirred at ambient temperature for about 1 h and then the reaction was quenched by a dropwise addition of water. EtOAc (100 mL) was added and the layers were separated. The organic phase was washed with water (75 mL), IN phosphoric acid (2×100 mL), water (100 mL), aqueous sodium bicarbonate (100 mL) and brine (100 mL) then dried over magnesium sulfate and concentrated to give (2R,4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-methylpyrrolidine-1-carboxylate that was used without further purification.

Provenance & Evidence