tert-Butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate → Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetate

HRID 1193331Notes

Reaction equation

HRID 1193331 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH3:2]>C(O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH3:2]

Participants

3

Reactant 1

HCID 10333298tert-Butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate

Product 1

HCID 9993342Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetateYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate (5.0 g, 18.58 mmol, 1 eq) was dissolved in ethanol (20 ml) and degassed for 30 min with nitrogen. Pd—C (500 mg, 10%) was added, and hydrogenation was carried out for 12 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Celite and washed with ethanol (200 ml), and the filtrate was concentrated under reduced pressure. Yield: 89% (4.5 g, 16.6 mmol).

Workup

  1. customdegassed for 30 min with nitrogen
  2. additionPd—C (500 mg, 10%) was added
  3. filtrationthe reaction mixture was filtered off over Celite
  4. washwashed with ethanol (200 ml)
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7658f16320904c6fa09fd50c0eecd499
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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