HCID 58237942, compound → HCID 44194657, compound

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).

1. customThe reaction mixture was quenched with aq NaHCO3 solution (5 mL)
2. customThe layers were separated
3. extractionThe aqueous layer was extracted with EtOAc (3×8 mL)
4. washThe combined organic phase was washed with a satd aq NaCl (5 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customto give the crude product, which
8. customwas purified by preparative HPLC

ORD record

ord-d49ce87504f7472f9d73ac0c65a22d1e

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680281B2