反応 #55448

反応方程式

1-(N-Benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-3,4-dihydroisoquinoline

sodium borohydride

→

1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

収率 37.7%

溶媒

ethanol

反応条件

後処理

1. 1
   その他was elevated to ambient temperature
2. 2
   ろ過An insoluble material was filtered off from the reaction mixture
3. 3
   濃縮the filtrate was concentrated under reduced pressure
4. 4
   workup.ADDITIONAfter water was added to the residue
5. 5
   抽出the mixture was extracted with ethyl acetate
6. 6
   洗浄The extract was washed with water
7. 7
   その他dried
8. 8
   workup.DISTILLATIONThe solvent was distilled off from the solution
9. 9
   洗浄washed with benzene
10. 10
    洗浄eluted with a mixture of chloroform and ethyl acetate
11. 11
    濃縮The eluate was concentrated
12. 12
    workup.ADDITIONthe residue was treated with ethanol
13. 13
    workup.ADDITIONcontaining hydrochloric acid
14. 14
    その他The crystals obtained
15. 15
    その他were recrystallized from a mixture of 99% ethanol and ether

実験手順

1-(N-Benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-3,4-dihydroisoquinoline (7.0 g) was added to 99% ethanol (160 ml) and to the solution was gradually added sodium borohydride (2.2 g) under ice cooling. The reaction temperature of the mixture was elevated to ambient temperature and the mixture was stirred for 3 hours. An insoluble material was filtered off from the reaction mixture and the filtrate was concentrated under reduced pressure. After water was added to the residue, the mixture was extracted with ethyl acetate. The extract was washed with water and dried. The solvent was distilled off from the solution and the residue was subjected to column chromatography on silica gel, washed with benzene and eluted with a mixture of chloroform and ethyl acetate. The eluate was concentrated and the residue was treated with ethanol containing hydrochloric acid. The crystals obtained were recrystallized from a mixture of 99% ethanol and ether to give 1-(N-benzyloxycarbonyl-p-chloroanilinomethyl)-6,7-dibenzyloxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.4 g), mp 139° to 142° C.

出典