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)
Workup
- temperatureunder reflux for 0.5 hours
- concentrationThe mixture was concentrated under vacuum the residue
- dissolutiondissolved in ethyl acetate
- washwashed with saturated sodium bicarbonate solution and brine
- customthe solvent evaporated
- customThe residue was purified by preparative silica gel TLC with 5% diethyl ether in dichlorometane
Sources & evidence
- ORD record
- ord-eb423ea980d045c09c5ce6b60efa76a4
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06191165B1
Reaction notes
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