Ethyl 4-piperidinecarboxylate → 1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

HRID 2356147Notes

Reaction equation

HRID 2356147 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>ClCCl.O>[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl isonipecotate (2.5 g, 15.9 mmol) in dichloromethane (80 mL) at 0° C. was treated with (BOC)2O (3.8 g, 17.3 mmol), warmed to room temperature, stirred for 2 hours, diluted with water, and extracted with dichloromethane. The combined extracts were washed sequentially with saturated sodium bicarbonate, 5% citric acid, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 258 (M+H)+.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined extracts were washed sequentially with saturated sodium bicarbonate, 5% citric acid, and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aa346d43f00d48e1832b67cc03633e07
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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