Tetrahydrofuran → Benzyl ethyl piperidine-1,3-dicarboxylate

HRID 408226Notes

Reaction equation

HRID 408226 reaction equation
[C:1](Cl)(=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1.C([O-])([O-])=O.[K+].[K+].C1COCC1>CCOCC.O>[N:12]1([C:1]([O:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:10])[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 98969Ethyl nipecotate

Product 1

HCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylateYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Benzyl carbonochloridate (4.5 mL, 31.7 mmol) at 0° C. was added to ethyl piperidine-3-carboxylate (5.0 g, 30.2 mmol) and K2CO3 (4.2 g, 30.2 mmol) in 1:1 THF:water (100 mL). The reaction mixture was stirred at room temperature for 2 hours, and then ether (50 mL) was added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography on silica gel (hexane:ethyl acetate, 5:1) to give 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (7.60 g 86% yield) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by chromatography on silica gel (hexane:ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-ea6e2c2d5eee45ceb9af1ce8dca9a547
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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