HCID 67498983, compound → HCID 67498962, compound

HRID 1919736Notes

Reaction equation

HRID 1919736 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) δ 4.16-4.08 (q, 2H), 3.93-3.83 (m, 2H), 2.36-2.28 (t, 2H), 2.04-1.08 (m, 20H); 13C NMR (62.7 MHz) 155.4 (s), 79.1 (s), 60.3 (s), δ 1.0 (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-502d3b1e4503439b9ac875ceaa77a809
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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