Tetrabutylammonium Fluoride → tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate (50 g) dissolved in tetrahydrofuran was added tetra-N-butylammonium fluoride (95 g) dissolved in tetrahydrofuran (250 mL) at 0° C. The mixture was stirred for 16 h at room temperature and then quenched with water (100 mL). The solution was washed with hydrochloric acid (6 N), extracted with ethyl acetate (3×100 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (2/1 petroleum ether/ethyl acetate) to afford tert-butyl (2S,4R)-4-hydroxy-2-(propan-2-yl)pyrrolidine-1-carboxylate.

Provenance & Evidence