Reaktion #81741

Reaktionsgleichung

Benzyl cis-4-amino-1-cyclohexanecarboxylate p-toluenesulphonate

(E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid

pyridine

thionyl chloride

triethylamine

→

oil

Ausbeute 93.9%

(E)-Benzyl cis-4-{1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxamido}-1-cyclohexanecarboxylate

Ausbeute 93.9%

Lösungsmittel

ethyl acetate

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 3 hours
2. 2
   Sonstigethe layers separated
3. 3
   WaschenThe ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of (E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid (1.0 g, 3.04 mmol) in ethyl acetate (10.6 mL) under a nitrogen atmosphere at room temperature was added dimethylformamide (1 drop), pyridine (0.49 mL, 6.08 mmol) and thionyl chloride (0.28 mL, 3.95 mmol) and the mixture stirred at room temperature for 40 minutes. Benzyl cis-4-amino-1-cyclohexanecarboxylate p-toluenesulphonate (1.29 g, 3.19 mmol) was added at room temperature followed by triethylamine (1.27 mL, 9.12 mmol) and the mixture stirred at room temperature for 3 hours. The reaction mixture was diluted with distilled water (50 mL) and ethyl acetate (50 mL) and the layers separated. The ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (1.552 g). The crude product was purified by chromatography on silica by elution with hexane/ethyl acetate (1:1) to give, after combination and evaporation of appropriate fractions, the title compound as an oil (1.07 g, 65%).

Quelle