반응 #216582
ord-9bcd66430d9a456faead55416dd089d9
반응 조건
후처리
- 1온도being maintained at <50° C
- 2기타The final reaction mixture
- 3온도was heated slowly
- 4온도to reflux for 45 minutes
- 5온도The mixture was cooled
- 6기타quenched with water
- 7추출the mixture was extracted with ethyl ether
- 8추출the resulting mixture was extracted 5 more times with methylene chloride
- 9기타The extract was dried
- 10기타the methylene chloride was evaporated
실험 절차
First, O-desmethyl tramadol was prepared as set forth hereinafter. Diethylene glycol (125 mL) was added with cooling to potassium hydride (9.5 g) with the temperature being maintained at <50° C. To the solution was added thiophenol (10 mL) dissolved in diethylene glycol (25 mL), and then (-)-tramadol as the free base (9.3 g) in diethylene glycol (50 mL) was added. The final reaction mixture was heated slowly to reflux for 45 minutes. The mixture was cooled and quenched with water. The pH was adjusted to about 3, and the mixture was extracted with ethyl ether. The pH was readjusted to about 8 and the resulting mixture was extracted 5 more times with methylene chloride. The extract was dried and the methylene chloride was evaporated to yield 4.6 g of the title compound. The title compound (4.6 g) was distilled (Kugelrohr), was dissolved in tetrahydrofuran and treated with an ethanol/HCl solution to give 2.3 g of the hydrochloride salt. The salt was recrystallized from ethanol/ethyl ether and dried to yield 1.80 g of the salt of the (-) enantiomer of O-desmethylated tramadol (mp. 242°-3° C.), [α]D25 =-32.9 (C=1, EtOH).