1,1-Dichloroethane → (4s,5r)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

To a solution of 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde (14.5 mg, 0.0291 mmol) in dichloroethane (300 μL) was added HNEt2 (4.6 μL, 0.0436 mmol), and NaBH(OAc)3 (9.2 mg, 0.0436 mmol). The reaction was stirred at room temperature for 18 hours and then diluted with EtOAc (10 mL) and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[(diethylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.57 (50% EtOAc/hexanes). LCMS=557.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.92 (s, 1H), 7.82 (s, 2H), 7.55-7.52 (m, 3H), 5.76 (d, J=8.0 Hz, 1H), 5.03 (d, J=16.1 Hz, 1H), 4.60 (d, J=16.1 Hz, 1H), 4.05-4.03 (m, 1H), 3.73 (d, J=13.5 Hz, 1H), 3.57 (d, J=13.7 Hz, 1H), 2.75-2.56 (m, 4H), 1.04 (bs, 6H), 0.80 (d, J=6.4 Hz, 3H).

Provenance & Evidence