Acetaldehyde → HCID 16658871, compound

Participants

Reaction Steps

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[(cyclobutylamino)methyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (3.6 mg, 6.50×10−3 mmol) in dichloroethane (300 μL) was added acetaldehyde (40 μL, 0.709 mmol) and NaBH(OAc)3 (excess). The reaction was stirred at room temperature for 2 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 (25% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-{[cyclobutyl(ethyl)amino]methyl}-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.69 (25% EtOAc/hexanes). LCMS=583.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.90 (s, 1H), 7.80 (s, 2H), 7.54-7.52 (m, 3H), 5.74 (d, J=8.0 Hz, 1H), 4.99 (d, J=16.1 Hz, 1H), 4.65 (d, J=16.2 Hz, 1H), 4.04-3.98 (m, 1H), 3.64 (d, J=13.9 Hz, 1H), 3.47 (d, J=13.9 Hz, 1H), 3.18-3.12 (m, 1H), 2.48-2.39 (m, 2H), 1.98-1.92 (m, 2H), 1.87-1.74 (m, 2H), 1.67-1.58 (m, 2H), 0.90 (t, J=7.2 Hz, 3H), 0.80 (d, J=6.6 Hz, 3H).

Provenance & Evidence