trans-N-Boc-2-methyl-6-(2-phenylethenyl)piperidine → trans-N-Boc-2-methyl-6-(2-phenylethyl)piperidine

HRID 840685Notes

Reaction equation

HRID 840685 reaction equation
[C:1]([N:8]1[C@@H:13]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH3:22])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:1]([N:8]1[C@@H:13]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH3:22])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 67499694trans-N-Boc-2-methyl-6-(2-phenylethenyl)piperidine

Product 1

HCID 67498981trans-N-Boc-2-methyl-6-(2-phenylethyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of trans-N-Boc-2-methyl-6-(2-phenylethenyl)piperidine (3.8, 12.54 mmol) in 6 mL of ethanol was shaken under 58 psi of H2 pressure over 0.70 g Pd/C catalyst overnight, and then the mixture was filtered through Celite and concentrated to give 3.81 g (quantitative) of the product. No further purification was necessary. 1H NMR (250 MHz)δ7.30-7.14 (m, 5 H), 3.93-3.89 (m, 2 H), 2.64-2.59 (t, 2 H), 1.98-1.20 (m, 20 H).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto give 3.81 g (quantitative) of the product
  4. customNo further purification

Sources & evidence

ORD record
ord-48ea873ee4484831a7aa13c9ba3f2c34
Source dataset
uspto-grants-2002_04
Patent number
US06369078B1

Reaction notes

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