Benzyl Bromide → 1-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate
Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)=[O:17])[CH3:14].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:13]([O:15][C:16]([C:18]1([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:20][CH2:19]1)=[O:17])[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirring solution of diisopropyl amine (38.0 mmol, 3.84 g) in THF (50 mL) cooled to -78° C. was added n-butyl lithium dropwise (41.2 mmol, 16.5 mL of a 1.6M solution in hexanes). To this was added piperidine-1,4-dicarboxylic acid tert-butyl ester ethyl ester (31.7 mmol, 8.16 g) in 20 mL THF. The reaction was allowed to stir for 5 min. and benzyl bromide (31.7 mmol, 5.42 g) was added. The reaction was then allowed to warm to room temperature. The reaction was then diluted with ethyl acetate (200 mL) and washed with 10% KHSO4. The aqueous layers were extracted with ethyl acetate (100 mL). The organics were combined, washed with brine and dried over anhydrous sodium sulfate. The solution was filtered and evaporated under reduced pressure to give 12.13 g of the title compound as a yellow oil.
Workup
- washwashed with 10% KHSO4
- extractionThe aqueous layers were extracted with ethyl acetate (100 mL)
- washwashed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe solution was filtered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6375f2715dde4a28ac8a75d35481e0fe
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05717100
Reaction notes
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