反応 #2021459

反応方程式

(−)-cocaine

→

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

収率 92.0%

溶媒

HCl

反応条件

後処理

1. 1
   温度(gentle reflux)
2. 2
   温度After cooling to room temperature
3. 3
   抽出the mixture was thoroughly extracted with ether
4. 4
   その他to remove the benzoic acid by-product
5. 5
   その他The acidic aqueous layer was evaporated on a rotary evaporator under high vacuum
6. 6
   workup.DISSOLUTIONthe residue was redissolved in water
7. 7
   その他to afford a white solid that
8. 8
   その他no further purification (92% yield)

実験手順

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).

出典