HCID 67498719, compound → HCID 22620176, compound

HRID 1919719Notes

Reaction equation

HRID 1919719 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([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][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 67498719HCID 67498719, compound

Product 1

HCID 22620176HCID 22620176, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-Boc-2-(1-heptenyl)piperdine (3.92, 13.93 mmol) in 7 mL of ethanol was shaken under 58 psi of H2 pressure over 0.78 g Pd/C catalyst overnight, and then the mixture was filtered through Celite and concentrated to give 3.94 g (quantitative) of the product. No further purification was necessary. 1H NMR (250 MHz) δ 4.20-4.15 (br s, 1H), 3.99-3.85 (br d, 1H), 2.79-2.70 (dt, 1H), 1.59-1.25 (m, 21H), 0.89-0.85 (t, 3H); 13C NMR (62.7 MHz) 155.1 (s), 78.8 (s), 50.3 (s), 38.6 (s), 31.8 (s), 29.6 (s), 29.5 (s), 29.3 (s), 28.4 (s), 26.3 (s), 25.6 (s), 22.6 (s), 18.9 (s), 14.0 (s) ppm.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto give 3.94 g (quantitative) of the product
  4. customNo further purification

Sources & evidence

ORD record
ord-0246af3fa7ff4c14afdcffda571262f9
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

Loading…