반응 #527691

반응 방정식

Sodium cyanoborohydride

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

methanol

formaldehyde

→

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

수율 77.6%

용매

acetic acid

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for a further 10 minutes
2. 2
   workup.STIRRINGstirred for 45 minutes
3. 3
   기타The methanol was removed in vacuo
4. 4
   workup.ADDITIONthe residue treated with aqueous sodium hydroxide solution
5. 5
   추출The product was extracted with ethyl acetate
6. 6
   세척The extracts were washed with aqueous ammonia solution, water and brine
7. 7
   건조dried over magnesium sulphate
8. 8
   농축Concentration

실험 절차

A mixture of 1-[1-(2-chlorophenyl)cyclopropyl]-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline (6.2 g), methanol (160 ml) and 37-40% aqueous formaldehyde solution was stirred for 15 minutes. Sodium cyanoborohydride (5.13 g) was added and the mixture was stirred for a further 10 minutes. The reaction was then neutralised with acetic acid and stirred for 45 minutes. The methanol was removed in vacuo and the residue treated with aqueous sodium hydroxide solution. The product was extracted with ethyl acetate. The extracts were washed with aqueous ammonia solution, water and brine, then dried over magnesium sulphate. Concentration yielded 1-[1-(2-chlorophenyl)cyclopropyl]-7-methoxy-2,6-dimethyl-1,2,3,4-tetrahydroisoquinoline as a gum (5.02 g).

출처