HCID 18727485, compound → HCID 18727478, compound

HRID 720888Notes

Reaction equation

HRID 720888 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:35])[CH:16]([CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:35])[CH:16]([CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 18727485HCID 18727485, compound

Product 1

HCID 18727478HCID 18727478, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

5-Phenyl-2-(3-phenyl-propyl)-pentanoic acid (1-benzyl-piperidin-4-yl)-amide (23) (0.5 g; 1.07 mmol) is combined with ethanol (25 mL) and 20% Pd(OH)2 on carbon (0.2 g) in a hydrogenation bottle. The mixture is hydrogenated at 50 psi for 18 hours then filtered through a celite pad and washed with ethanol. The combined filtrate plus wash is concentrated in vacuo affording the desired product (0.38 g) as an oil. ESMS:MH+ 379.4 (base).

Workup

  1. filtrationthen filtered through a celite pad
  2. washwashed with ethanol
  3. washThe combined filtrate plus wash
  4. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-13689bb15fad46fea7d21735716bc714
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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