Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 178471542, compound

HRID 967154Notes

Reaction equation

HRID 967154 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]=O)[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:22][C:23](=[O:44])[CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:21]>ClCCl>[CH2:20]([O:22][C:23](=[O:44])/[CH:24]=[CH:17]/[C@H:14]1[CH2:15][CH2:16][C@H:11]([CH2:10][CH2:9][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])[CH3:8])[CH2:12][CH2:13]1)[CH3:21]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 178483647HCID 178483647, compound

Product 1

HCID 178471542HCID 178471542, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.02 g (14.9 mmol) trans-[2-(4-formyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester and 5.47 g (14.9 mmol) of (triphenyl-phosphoranylidene)-acetic acid ethyl ester in 40 ml of dichloromethane was stirred at room temperature for 60 hours. After concentration under reduced pressure, the crude product was chromatographed on silica gel with a 9:1 v/v mixture of hexane and ethylacetate as the eluent giving 3.82 g (75.4%) of pure trans-3-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-(E)-acrylic acid ethyl ester as colorless viscous oil, MS: 340 (MH+).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe crude product was chromatographed on silica gel with a 9:1 v/v mixture of hexane and ethylacetate as the eluent

Sources & evidence

ORD record
ord-f64d0ed41853439693c13d2b76f548cd
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

Loading…