Cyclohexene → 3-(2-Chloroethyl)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one

Participants

Reaction Conditions

Reaction Steps

A stirring mixture of 1-(4-fluorophenyl)-3-(2-chloroethyl)-4-[4-(benzyloxy)phenyl]azetidin-2-one (prepared according to Bioorg. Med. Chem. Lett. 1996, 6, 1271-1274; 2.00 g, 4.88 mmol), Pd(OH)2/C (0.500 g, 20%) and cyclohexene (6 ml) in MeOH (60 ml) was heated to 70° C. After 2 hours, the reaction mixture was cooled to room temperature and was filtered through diatomaceous earth. The solvent was removed under reduced pressure to give the title compound (1.57 g; -quantitative yield). No further purification was necessary. NMR (CD3OD, 400 MHz) 2.20-2.40 (m, 2H), 3.20-3.40 (m, 1H), 3.70 (t, 2H), 4.85 (d, 1H), 6.75-6.80 (m, 2H), 6.90-7.00 (m, 2H), 7.15-7.30 (m, 4H); m/z: 320.0.

Provenance & Evidence