HCID 69799108, compound → HCID 22496088, compound

HRID 1816008Notes

Reaction equation

HRID 1816008 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 69799108HCID 69799108, compound

Product 1

HCID 22496088HCID 22496088, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-(4-benzyloxyphenyl)-3-(pyridin-3-yl)but-2-enoate (1.73 mmole) and 10% Pd/C (200 mg) in EtOH (10 mL) was shaken under H2 (50 psi) on a Parr apparatus. After 4 hr, the mixture was filtered through celite®d and the filtrate was concentrated. Flash chromatography on silica gel (50% EtOAc/hexanes) gave the impure title compound (327 mg, 66% over three steps) as a yellow oil: MS (ES) m/e 286 (M+H)+. This material was used without further purification.

Workup

  1. filtrationthe mixture was filtered through celite®d
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f29f664606ff4932941a59aaefa6b48d
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

Loading…