Sodium hydride → HCID 118117552, compound

Participants

Reaction Conditions

Reaction Steps

NaH 60% Dispersion in mineral oil (0.93 g, 23.2 mmol) was added portionwise to a 0° C. solution of 2-chloro-N—[(R)-1-hydroxymethyl-2-(3-iodo-phenyl)-ethyl]-acetamide A-9 (3.72 g, 10.5 mmol) in THF (100 mL) under argon and the resulting suspension was warmed to RT and stirred for 1 h. The reaction mixture was cooled back to 0° C. before being quenched with water and concentrated in vacuo. The remaining aqueous phase was extracted with DCM (3×) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 50% to 100% EtOAc in hexane) to give the title compound as a white solid. LC-MS B: tR=0.72 min; [M+H+MeCN]+=359.01; 1H NMR (CDCl3) δH: 7.64 (d, J=7.9 Hz, 1H), 7.59 (s, 1H), 7.18 (m, 1H), 7.10 (t, J=7.7 Hz, 1H), 6.25 (s, 1H), 4.20 (s, 2H), 3.91 (dd, J1=11.7 Hz, J2=3.7 Hz, 1H), 3.76 (m, 1H), 3.60 (dd, J1=11.7 Hz, J2=6.1 Hz, 1H), 2.87 (dd, J1=13.6 Hz, J2=6.0 Hz, 1H), 2.72 (dd, J1=13.6 Hz, J2=8.5 Hz, 1H).

Provenance & Evidence