Réaction #44497

Équation de réaction

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

Solvants

CH3CN

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.ADDITIONwere added
3. 3
   TempératureThen, heating
4. 4
   AutreThe solvent was evaporated
5. 5
   Autrethe residue was partitioned with diethyl ether and water
6. 6
   LavageThe organic phase was washed with a NaHCO3 solution until the washes
7. 7
   AutreIt was then dried
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated
10. 10
    AutreThe residue was purified over silica gel using 2-30% diethyl ether in hexanes

Mode opératoire

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.

Source