2,3-Dibromopropene → 1-Tert-butyl 4-ethyl 4-(2-bromoallyl)piperidine-1,4-dicarboxylate
Reaction equation
C([N-]C(C)C)(C)C.[Li+].[N:9]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1.[Br:27][C:28]([CH2:30]Br)=[CH2:29].[NH4+].[Cl-]>C1COCC1>[Br:27][C:28](=[CH2:29])[CH2:30][C:12]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10][N:9]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:14][CH2:13]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Lithium diisopropylamide (29.1 mL, 58.3 mmol) was added dropwise at −78° C. To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (9.56 mL, 38.9 mmol) in THF (200 mL), and stirred at this temperature for 50 min. 2,3-Dibromoprop-1-ene (5.47 mL, 56.0 mmol) in THF (10 mL) was added to the reaction mixture slowly and the resulting mixture was stirred for 1.5 hr at −78° C. The reaction mixture was queched with NH4Cl solution (15 mL) and was allowed to warm to room temperature and the aqueous layer was extracted with EtOAc (30 mL×3). The combined organics were washed with brine (30 mL), dried over MgSO4 and concentrated to get the crude product which was purified by silica gel column chromatography (RediSep 220 g Gold column) using (0-30) % EtOAc/Hexanes as mobile phase to give the title compound.
Workup
- temperatureto warm to room temperature
- extractionthe aqueous layer was extracted with EtOAc (30 mL×3)
- washThe combined organics were washed with brine (30 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
- customto get the crude product which
- customwas purified by silica gel column chromatography (RediSep 220 g Gold column)
Sources & evidence
- ORD record
- ord-7463efeede7244a0ba10dad9368269a7
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206198B2
Reaction notes
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