HCID 86607883, compound → HCID 68817632, compound

HRID 736748Notes

Reaction equation

HRID 736748 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7](CC(C=C)=CC)[CH2:8][CH2:9][C:10]=1[NH:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])=[O:4]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH2:6][NH:7][CH2:8][CH2:9][C:10]=1[NH:11][CH:12]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:13])=[O:4]

Participants

4

Reactant 1

HCID 86607883HCID 86607883, compound

Product 1

HCID 68817632HCID 68817632, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(1-phenyl-ethyl amino)-1-(2-vinyl-but-2-enyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (6.0 g, 17.02 mmol) and 20% palladium hydroxide on carbon (2 g) in methanol (20 mL) was stirred under a hydrogen balloon for 19 h. The mixture was then filtered through a thin pad of celite and concentrated to provide 4-(1-phenyl-ethylamino)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester as a colorless oil (4.5 g, 90%). MS: 261 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through a thin pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-349a24f3177c49808bbca8ee864455d4
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…