Sodium hydride → HCID 67479956, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (1.10 g, 5.89 mmol) and 2,3,5-trifluoropyridine (0.86 g, 6.48 mmol) in dry THF (20 mL) and dry DMF (4 mL), at rt was added 60% NaH in oil (0.35 g, 8.84 mmol). The mixture was stirred in a 40° C. oil bath overnight, cooled to rt, diluted with ether (175 mL), washed with water (25 mL) and brine (25 mL), and dried over Na2SO4. Removal of the solvent left a dark oil (1.94 g) which was purified by chromatography on a 40-g silica cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (R)-tert-butyl 3-(3,5-difluoropyridin-2-yloxy)pyrrolidine-1-carboxylate (0.83 g, 47%). LC-MS Method 1 tR=1.85 min, m/z=301.

Provenance & Evidence