HCID 67498933, compound → HCID 22620198, compound

HRID 840683Notes

Reaction equation

HRID 840683 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1/[CH:14]=[CH:15]\[CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 67498933HCID 67498933, compound

Product 1

HCID 22620198HCID 22620198, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the 1.5 g (6.66 mmol) of N-Boc-2-(cis-1-propenyl)piperdine in 2 mL of ethanol was shaken under 58 psi H2 pressure over 0.3 g Pd/C catalyst overnight, and then the mixture was filtered through Celite and concentrated to give 1.43 g (94%) of the product as a clear colorless oil. No further purification was necessary. 1H NMR (250 MHz) δ4.21-4.17 (br s, 1 H), 3.98-3.92 (br d, I H), 2.79-2.68 (dt, 1 H), 1.67-1.23 (m, 19 H), 0.93-0.88 (t, 3 H); 13C NMR (62.7 MHz) 155.1 (s), 78.9 (s), 50.0 (s), 38.6 (s), 31.8 (s), 28.4 (s), 25.6 (s), 19.1 (s), 18.9 (s), 14.0 (s) ppm.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-34d56d2d53e14350973ea6401ce33f03
Source dataset
uspto-grants-2002_04
Patent number
US06369078B1

Reaction notes

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