Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate → Tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[C].[Pd]>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate (848.0 mg, 2.144 mmol) in ethyl acetate (45 ml) was added 5% palladium carbon (84.5 mg, 50% containing water), and the mixture was hydrogenated at room temperature, under atmospheric pressure for 11 hrs. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=6:4→7:3) to give tert-butyl 4-(6-{2-[4-(hydroxymethyl)phenyl]ethyl}pyridin-3-yl)piperazine-1-carboxylate (716.9 mg, yield 84.1%) as a white solid.
Workup
- filtrationThe reaction mixture was filtered through Celite
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=6:4→7:3)
Sources & evidence
- ORD record
- ord-7f98ae0a48524e549174f13142cf7a81
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999989B2
Reaction notes
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