Reacción #2383790

Ecuación de reacción

diethyl ether

Allyl (8S,9R)-10-((E)-ethylidene)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate

triphenylphosphine

sodium 2-ethylhexanoate

→

title compound

Rendimiento 47.0%

Sodium (8S,9R)-10-((E)-ethylidene)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate

Rendimiento 47.0%

Disolventes

tetrahydrofuran dichloromethane

tetrahydrofuran dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturait was cooled to the temperature of 0° C
2. 2
   FiltraciónThe separated product was filtered off
3. 3
   Lavadowashed with an anhydrous mixture of diethyl ether/tetrahydrofuran
4. 4
   Otrodried in vacuo

Procedimiento

Allyl (8S,9R)-10-((E)-ethylidene)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate (73 mg; 0.267 mmole) prepared according to the process disclosed in Example 11a was dissolved in a mixture (0.5 ml) of tetrahydrofuran/dichloromethane 1:1 (v/v). To the obtained mixture there were added first a solution of triphenylphosphine (24 mg; 0.08 mmole) and then a solution of sodium 2-ethylhexanoate (46.8 mg; 0.28 mmole) and tetrakis(triphenylphosphine)palladium(0) (32 mg; 0.024 mmole) (prepared according to the process disclosed in D. R.Coulson, Inorganic Synthesis 13, 121 (1972)) in a mixture (2 ml) of tetrahydrofuran/dichloromethane (1:1). The obtained solution was stirred for 30 minutes at room temperature. To the obtained mixture diethyl ether (4 ml) was added and it was cooled to the temperature of 0° C. The separated product was filtered off, washed with an anhydrous mixture of diethyl ether/tetrahydrofuran and dried in vacuo. The title compound (32 mg; 47%) was obtained in the form of brownish crystals and with m.p. 222-225° C. with decomposition (DMF-diethyl ether).

Fuente