Boron tribromide → HCID 59485911, compound

Participants

Reaction Conditions

Reaction Steps

(4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(hydroxymethyl)-4-(3-methoxyphenyl)oxazolidin-2-one (Example 91) was dissolved in dichlormethane, cooled to −78° C., and treated with boron tribromide (1M solution, 2.1 eq). After 10 min, the cooling bath was removed, and the reaction mixture is stirred for 1 h. The reaction was then quenched with water, extracted with ethyl acetate, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel (2-5% methanol/dichlormethane) to give the title compound. 1H NMR (acetone-d6) δ (ppm) 8.36 (s, 1H), 7.42 (d, J=9.1 Hz, 2H), 7.23 (d, J=9.0 Hz, 2H), 7.09 (t, J=7.9 Hz, 1H), 6.85-6.81 (m, 4H), 6.77 (d, J=7.6 Hz, 1H), 6.74 (m, 1H), 6.67 (dd, J=8.1, 2.4 Hz, 1H), 5.39 (d, J=5.2 Hz, 1H), 4.49 (t, J=5.9 Hz, 1H), 4.36 (ddd, J=5.6, 3.7, 3.4), 3.96 (ddd, J=12.4, 5.7, 3.6 Hz, 1H), 3.85 (ddd, J=12.3, 5.6, 3.8 Hz, 1H); HPLC-MS calculated C22H18ClNO5 (M+H+): 411.1, found: 410.0.

Provenance & Evidence