Triethylamine → cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate
Reaction equation
C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.CC1CCNCC1C(OCC)=O.C(N(CC)CC)C.[CH3:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]>ClCCl>[CH3:35][C@H:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:46])[CH3:47])=[O:43])[CH2:38][C@H:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Di-tert-butyl dicarbonate (3.26 g, 15.20 mmol) was added to a solution of ethyl 4-methylpiperidine-3-carboxylate (2.0 g, 11.68 mmol) and triethylamine (3.9 mL, 28.05 mmol) in anhydrous dichloromethane (50 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The mixture partitioned between dichloromethane and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a mixture of the cis and trans diastereomers of 1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (3.0 g). The crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether) to afford cis-1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (2.5 g).
Workup
- customThe mixture partitioned between dichloromethane and water
- dry with materialThe organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto afford
- customThe crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-4a634299e5f74e8d8bc683344d04df11
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296745B2
Reaction notes
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