HCID 67498983, compound → HCID 67498962, compound

HRID 840700Notes

Reaction equation

HRID 840700 reaction equation
[C:1]([N:8]1[C@@H:13]([C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH3:20])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:1]([N:8]1[C@@H:13]([C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH3:20])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 67498983HCID 67498983, compound

Product 1

HCID 67498962HCID 67498962, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of trans-N-Boc-2-methyl-6-(ethenyl propionyl)piperidine (2.0 g, 6.70 mmol) in 3 mL of ethanol was shaken under 58 psi of H2 pressure over 0.65 g Pd/C catalyst overnight, and then the mixture was filtered through Celite and concentrated to give 1.8 g (90%) of the product which was homogeneous by TLC analysis. 1H NMR (250 MHz) δ4.16-4.08 (q, 2 H), 3.93-3.83 (m, 2 H), 2.36-2.28 (t, 2 H), 2.04-1.08 (m, 20 H); 13C NMR (62.7 MHz) 155.4 (s), 79.1 (s), 60.3 (s), 51.0 (s), 47.2 (s), 31.9 (s), 29.6 (s), 28.5 (s), 26.9 (s), 25.8 (s), 24.2 (s), 20.5 (s), 14.2 (s), ppm.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bb8c54ee850542fd8fb48ebb8461af2c
Source dataset
uspto-grants-2002_04
Patent number
US06369078B1

Reaction notes

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