Reacción #44497

Ecuación de reacción

3-Bromo-2-bromomethyl-propionic acid methyl ester

1-cyclohex-1-enyl-pyrrolidine

triethyl amine

acetic acid

→

title compound

9-Oxo-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Disolventes

CH3CN

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.ADDITIONwere added
3. 3
   TemperaturaThen, heating
4. 4
   OtroThe solvent was evaporated
5. 5
   Otrothe residue was partitioned with diethyl ether and water
6. 6
   LavadoThe organic phase was washed with a NaHCO3 solution until the washes
7. 7
   OtroIt was then dried
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated
10. 10
    OtroThe residue was purified over silica gel using 2-30% diethyl ether in hexanes

Procedimiento

3-Bromo-2-bromomethyl-propionic acid methyl ester (30 g, 115 mmol) was added to a stirred solution of freshly distilled 1-cyclohex-1-enyl-pyrrolidine (20.4 mL, 126 mmol) and triethyl amine (35 mL, 252 mmol) in dry CH3CN (400 mL). After the addition, the mixture was heated (100° C.) and stirred for twelve hours before acetic acid (20 mL) and water (100 mL) were added. Then, heating was continued for another three hours. The solvent was evaporated and the residue was partitioned with diethyl ether and water. The organic phase was washed with a NaHCO3 solution until the washes became basic. It was then dried, filtered, and evaporated. The residue was purified over silica gel using 2-30% diethyl ether in hexanes to give the title compound as a clear oil.

Fuente