HCID 68708089, compound → HCID 18442924, compound

HRID 1434599Notes

Reaction equation

HRID 1434599 reaction equation
[C:1]1([C:7]([CH:14]2[CH2:19][CH2:18][N:17]([O:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)=[CH:8][C:9](OCC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C>[CH3:3][CH2:2][CH2:1][CH:7]([CH3:14])[CH3:8].[C:1]1([CH:7]([CH:14]2[CH2:19][CH2:18][N:17]([O:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)[CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 68708089HCID 68708089, compound

Product 2

HCID 78922-MethylpentaneHCID 18442924HCID 18442924, compoundYield 133.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-phenyl-3-(1-tert-butylcarbonyloxypiperidin-4-yl)acrylate (˜25 mmol) was dissolved in ethanol (200 mL) and the solution purged with argon. 20% Palladium hydroxide (2 g) was added and the resulting mixture was stirred at room temperature under an atmosphere of hydrogen (balloon) for 72 h. The mixture was purged with argon, filtered and the filtrate evaporated. The crude product was purified by silica gel chromatography (eluent:isohexane then 35% ethyl acetate in isohexane) to give the sub-titled compound (5.3 g).

Workup

  1. customthe solution purged with argon
  2. addition20% Palladium hydroxide (2 g) was added
  3. customThe mixture was purged with argon
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe crude product was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-d0634c6f83cc4c33bc6e6ec7073ae9cf
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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