N-[3-(4-chlorophenyl)-3-(4-fluorophenyl)3-hydroxypropyl]pipecolic acid methyl ester → N-[3-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-enyl]pipecolic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[CH2:10][CH2:11][C:12]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)O>C(O)=O>[CH3:1][O:2][C:3](=[O:28])[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[CH2:10][CH:11]=[C:12]([C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1Participants
3
Procedure
A solution of 0.035 g (0.086 mmol) N-[3-(4-chlorophenyl)-3-(4 fluorophenyl)-3-hydroxypropyl]pipecolic acid methyl ester (Compound B30) in 1 ml 99% formic acid was heated under reflux for 0.5 hours. The mixture was concentrated under vacuum the residue dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and brine, and the solvent evaporated. The residue was purified by preparative silica gel TLC with 5% diethyl ether in dichlorometane to give 0.018 g (yield 54%) N-[3-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-enyl]pipecolic acid methyl ester (Compound B20)