반응 #527705

반응 방정식

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

수율 71.7%

용매

methanol

반응 조건

후처리

1. 1
   온도to warm to ambient temperature
2. 2
   농축The reaction mixture was concentrated
3. 3
   기타the residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution
4. 4
   세척The organic phase was washed with aqueous ammonia solution
5. 5
   기타dried
6. 6
   농축concentrated

실험 절차

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).

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