1-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-enyl)piperidine → 1-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylpropyl)piperidine

HRID 278221Notes

Reaction equation

HRID 278221 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[CH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 570744891-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-enyl)piperidine

Product 1

HCID 181874541-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylpropyl)piperidineYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-en-1-yl)piperidine from Step A (0.95 g, 2.7 mmol) was hydrogenated using 5% Pd/C (10 mg) in 95% ethanol (20 mL) at atmospheric pressure. After 3.5 h, the mixture was filtered and the catalyst was washed with 95% ethanol. Evaporation of the filtrate gave 0.95 g of 1-(benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-yl)piperidine as a colorless syrup.

Workup

  1. filtrationthe mixture was filtered
  2. washthe catalyst was washed with 95% ethanol
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-c5f1c37f7b904bdb9d422256d6941e04
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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