반응 #527677

반응 방정식

hydrobromic acid

formaldehyde

sodium cyanoborohydride

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

→

7-benzyloxy-6-methoxy-2-methyl-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 (100 ml)
2. 2
   추출extracted with dichloromethane (300 ml)
3. 3
   세척The extract was washed with dilute aqueous ammonia solution
4. 4
   기타to yield a residue which
5. 5
   기타The solvent was removed by evaporation

실험 절차

A mixture of 7-benzyloxy-6-methoxy-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline. (1.89 g), 37% aqueous formaldehyde solution (3 ml), methanol (30 ml) and sodium cyanoborohydride (0.5 g) was stirred at ambient temperature for 24 hours. The mixture was poured onto water (100 ml) and extracted with dichloromethane (300 ml). The extract was washed with dilute aqueous ammonia solution to yield a residue which was dissolved in propan-2-ol and treated with 48% aqueous hydrobromic acid. The solvent was removed by evaporation to yield 7-benzyloxy-6-methoxy-2-methyl-1-[1-(2-methylthiophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinoline which was used without further purification.

출처