Ethyl Acrylate → Tert-butyl 1'-(2-ethoxycarbonyl-ethyl)-[4,4']bipiperidinyl-1-carboxylate

HRID 599732Notes

Reaction equation

HRID 599732 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[N:8]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1>CCO>[CH2:6]([O:5][C:1]([CH2:2][CH2:3][N:17]1[CH2:16][CH2:15][CH:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13][CH2:12]2)[CH2:19][CH2:18]1)=[O:4])[CH3:7]

Participants

4

Reactant 2

HCID 8821Ethyl Acrylate2×HCID 117475994,4'-Bipiperidine, 1-boc protected

Product 1

HCID 68690102Tert-butyl 1'-(2-ethoxycarbonyl-ethyl)-[4,4']bipiperidinyl-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 mL (40.6 mmol) ethyl acrylate were added to a solution of 10.0 g (37.3 mmol) tert.butyl [4,4′]bipiperidinyl-1-carboxylate in 100 mL EtOH and the reaction mixture was refluxed for 2 h. To complete the reaction a further 1 mL (9.2 mmol) ethyl acrylate were added, the mixture was refluxed for 1 h and left overnight at RT. The solvent was eliminated i.vac. and the crude product was further reacted without any purification.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. additionwere added
  3. temperaturethe mixture was refluxed for 1 h

Sources & evidence

ORD record
ord-f0827097618d49b2b8ebaef2da53213e
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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