Sodium hydride → HCID 86682284, compound

Participants

Reaction Steps

To a solution of benzyl ((1R,2S)-1-(3-chloro-4-methoxyphenyl)-1-hydroxypropan-2-yl)carbamate (0.24 g, 0.686 mmol) in THF (4.6 mL) was added NaH (0.036 g, 0.892 mmol) at 0° C. The reaction mixture was warmed to RT and stirred overnight. It was then quenched with 1N HCl (1.5 mL). This mixture was diluted with EtOAc and washed with sat. aqueous NaHCO3, water and brine. The organic phase was dried with Na2SO4 and concentrated. The residue was purified by silica gel chromatography, eluted with EtOAc to give (4S,5R)-5-(3-chloro-4-methoxyphenyl)-4-methyloxazolidin-2-one (intermediate K, 0.13 g). 1H NMR (500 MHz, CDCl3): δ 7.37 (s, 1H), 7.21 (d, 1H), 6.97 (d, 1H), 5.84 (b, 1H), 5.65 (d, 1H), 4.21 (m, 1H), 3.96 (s, 3H), 0.87 (d, 3H).

Provenance & Evidence