Acetaldehyde → HCID 24896151, compound

Participants

Reaction Steps

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[1-(isopropylamino)propyl]-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (28.5 mg, 0.0500 mmol) in dichloroethane (1 mL) was added acetaldehyde (2 mL) and NaBH(OAc)3 (excess). The reaction was stirred at room temperature for 16 hours, and then diluted with EtOAc (10 mL) and washed with water and brine (5 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification by PTLC (50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2 {1-[ethyl(isopropyl)amino]propyl}-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.53 (50% EtOAc/hexanes). LCMS=599.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.90 (s, 1H), 7.81 (s, 2H), 7.56-7.49 (m, 3H), 5.78-5.74 (m, 1H), 5.02 (d, J=16.4 Hz, 1H), 4.74-4.71 (m, 1H), 4.07-4-04 (m, 1H), 3.90-3.87 (m, 1H), 2.89-2.85 (m, 1H), 2.62-2.52 (m, 2H), 2.00-1.96 (m, 1H), 1.79-1.72 (m, 1H), 1.26-0.69 (m, 15H).

Provenance & Evidence