HCID 178457346, compound → HCID 178457345, compound

Participants

Reaction Steps

To a solution of (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](propyl)amino]methyl}cyclohexyl)acetic acid (8.8 mg, 0.0126 mmol) in THF (1 mL) was added a 1 M solution of BH3 in THF (75 μL, 0.075 mmol). The reaction was stirred at room temperature for 2 hours and then quenched with water (5 mL), diluted with EtOAc (15 mL), and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (10 to 50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[{[trans-4-(2-hydroxyethyl)cyclohexyl]methyl}(propyl)amino]-5-(trifluoromethoxy)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.09 (25% EtOAc/hexanes). LCMS=685.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89 (s, 1H), 7.78 (s, 2H), 7.16 (d, J=8.9 Hz, 2H), 7.10 (d, J=8.8 Hz, 1H), 5.74 (d, J=8.0 Hz, 1H), 4.72 (d, J=16.4 Hz, 1H), 4.58 (d, J=16.4 Hz, 1H), 4.02-3.98 (m, 1H), 3.66-3.64 (m, 2H), 2.77-2.73 (m, 4H), 1.77-0.81 (m, 17H), 0.64 (d, J=6.6 Hz, 3H).

Provenance & Evidence