Dimethyl Sulfoxide → 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid methyl ester

温度

70 °C

To a solution of trifluoro-methanesulfonic acid 4-[1-benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-phenyl ester (10.0 g, 19.8 mmol) in a Parr pressure bottle in MeOH (69 mL) were added DMSO (62 mL) and triethylamine (21.8 mL, 157 mmol). To the reaction mixture were added palladium acetate (2.2 g, 9.1 mmol) and 1,3-bis(diphenylphosphino)propane (3.75 g, 9.1 mmol). The mixture was shaken under 40 psi of CO at 70° C. for 4 hours. The reaction mixture was cooled to room temperature and was diluted with diethyl ether (600 mL). The ether layer was washed with water (5×60 mL), dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography with hexanes/EtOAc (1:1) to afford 6.9 g (85% yield) of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzoic acid methyl ester. 1HNMR (400 MHz, CDCl3) δ 7.91 (d, 2H), 7.32 (d, 2H), 7.28-7.16 (comp, 6H),), 6.82 (d, , 1H), 6.79 (s, 1H), 6.68 (dd, 1H), 3.86 (s, 3H), 3.74 (s, 3H), 3.38 (s, 2H), 2.47-2.44 (comp, 8H); MS (M+1) 416.2.

1. temperatureThe reaction mixture was cooled to room temperature
2. washThe ether layer was washed with water (5×60 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated
5. customThe crude residue was purified by flash chromatography with hexanes/EtOAc (1:1)

ORDレコード

ord-73e49a697f9e449a8dd1348f7706770e

出典データセット

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06720336B2