Reaktion #527705

Reaktionsgleichung

sodium cyanoborohydride

1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline

formaldehyde

→

1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-2,6-dimethyl-1,2,3,4-tetrahydroisoquinoline

Ausbeute 71.7%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   Sonstigethe residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution
4. 4
   WaschenThe organic phase was washed with aqueous ammonia solution
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated

Vorschrift

A mixture of the oxalate salt of 1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline (4.42 g prepared as described in Example RC12), methanol (87 ml) and 37-40% aqueous formaldehyde solution (5.1 ml) was cooled to 10° C. and sodium cyanoborohydride (2.64 g) was added. After 10 minutes the mixture was allowed to warm to ambient temperature and was stirred for 24 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution. The organic phase was washed with aqueous ammonia solution, then dried and concentrated to yield 1-[1-(2-chlorophenyl)cyclobutyl]-7-methoxy-2,6-dimethyl-1,2,3,4-tetrahydroisoquinoline (3.3 g).

Quelle