Reacción #2021459

Ecuación de reacción

(−)-cocaine

→

[1R-(exo,exo)]-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Rendimiento 92.0%

Disolventes

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperatura(gentle reflux)
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   Extracciónthe mixture was thoroughly extracted with ether
4. 4
   Otroto remove the benzoic acid by-product
5. 5
   OtroThe acidic aqueous layer was evaporated on a rotary evaporator under high vacuum
6. 6
   workup.DISSOLUTIONthe residue was redissolved in water
7. 7
   Otroto afford a white solid that
8. 8
   Otrono further purification (92% yield)

Procedimiento

Commercially available (−)-cocaine (Sigma Chemical Co.) was dissolved in 1.25 M HCl (1 g cocaine/12 ml). The mixture was allowed to stir for 16 hours at 110-115° C. (gentle reflux). After cooling to room temperature, the mixture was thoroughly extracted with ether to remove the benzoic acid by-product. The acidic aqueous layer was evaporated on a rotary evaporator under high vacuum and then the residue was redissolved in water and lyophilized to afford a white solid that required no further purification (92% yield).

Fuente