HCID 58237942, compound → HCID 44194657, compound

Participants

Reaction Steps

To a solution of (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-oxopropyl)-4-phenyl piperidin-2-one (82 mg, 0.2 mmol) in anhydrous THF (20 mL) was added dropwise methylmagnesium bromide (0.4 mL, 3M) at −78° C. under nitrogen. The formed mixture was stirred at rt for 1 h. The reaction mixture was quenched with aq NaHCO3 solution (5 mL). The layers were separated. The aqueous layer was extracted with EtOAc (3×8 mL). The combined organic phase was washed with a satd aq NaCl (5 mL), dried over Na2SO4 and concentrated in vacuo to give the crude product, which was purified by preparative HPLC to afford (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-hydroxy-2-methylpropyl)-4-phenylpiperidin-2-one (60 mg, 70.5%). LC-MS Method 2, tR=2.131 min, m/z=454. 1H NMR (CDCl3): δ 0.85 (s, 3H), 1.05 (s, 3H), 1.46 (m, 3H), 1.85-1.89 (m, 1H), 1.96-2.18 (m, 4H), 2.73-2.76 (m, 1H), 2.89-2.94 (m, 1H), 3.58-3.63 (m, 1H), 5.91-5.96 (m, 1H), 6.95-6.97 (m, 1H), 7.21-7.34 (m, 7H).

Provenance & Evidence