Reaktion #527677

Reaktionsgleichung

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

Lösungsmittel

methanol

propan-2-ol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe mixture was poured onto water (100 ml)
2. 2
   Extraktionextracted with dichloromethane (300 ml)
3. 3
   WaschenThe extract was washed with dilute aqueous ammonia solution
4. 4
   Sonstigeto yield a residue which
5. 5
   SonstigeThe solvent was removed by evaporation

Vorschrift

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.

Quelle