Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 1-{1-[4-(2-Methoxycarbonylvinyl)benzoyl]-4-piperidinyl]-3,4-dihydrocarbostyril

HRID 1648580Notes

Reaction equation

HRID 1648580 reaction equation
[CH:1]([C:3]1[CH:27]=[CH:26][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)=O.[C:28]([CH:32]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:30][CH3:31])=[O:29]>CO>[CH3:31][O:30][C:28]([CH:32]=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:26][CH:27]=1)=[O:29]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 190308281-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril

Product 1

HCID 537359061-{1-[4-(2-Methoxycarbonylvinyl)benzoyl]-4-piperidinyl]-3,4-dihydrocarbostyrilYield 145.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (4.77 g) is dissolved in methanol (100 ml) and thereto is added carbomethoxymethylenetriphenylphosphorane (5.3 g) and the mixture is stirred at room temperature for 1 hour. The solvent is concentrated and the residue is purified roughly by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to give a mixture (8 g) of 1-{1-[4-(2-methoxycarbonylvinyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril and triphenylphosphineoxide.

Workup

  1. concentrationThe solvent is concentrated
  2. customthe residue is purified roughly by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-85d8cf1495314ec2b2859bf2226057a8
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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