반응 #527676

반응 방정식

hydrobromic acid

Sodium cyanoborohydride

7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-3,4-dihydroisoquinoline

acetic acid

→

7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline

용매

methanol

propan-2-ol

반응 조건

후처리

1. 1
   workup.ADDITIONThe mixture was poured onto water (300 ml)
2. 2
   추출extracted with dichloromethane
3. 3
   세척The organic layer was washed with aqueous ammonia solution (100 ml)
4. 4
   건조brine (100 ml), and dried over magnesium sulphate
5. 5
   기타The solvent was removed by evaporation
6. 6
   기타to yield a gum
7. 7
   기타Evaporation of the solvent
8. 8
   기타yielded a solid which
9. 9
   기타was triturated with petroleum ether (b.p. 60°-80° C.)
10. 10
    기타isolated by filtration

실험 절차

Sodium cyanoborohydride (0.8 g) was added to a mixture of 7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-3,4-dihydroisoquinoline (2.8 g, prepared as described in Example CA32), acetic acid (20 ml) and methanol (10 ml) at 0° C. and stirred for 60 hours at ambient temperature. The mixture was poured onto water (300 ml) and extracted with dichloromethane. The organic layer was washed with aqueous ammonia solution (100 ml), then brine (100 ml), and dried over magnesium sulphate. The solvent was removed by evaporation to yield a gum. The gum was dissolved in propan-2-ol and treated with excess 48% aqueous hydrobromic acid. Evaporation of the solvent yielded a solid which was triturated with petroleum ether (b.p. 60°-80° C.), then isolated by filtration to give 7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline.

출처