反应详情

A stirred solution of 200 ml of 0.5 M borane/THF was treated with N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (11.5 g, 0.03 m) portionwise, at room temperature, then warmed to reflux. After 30 min at reflux, the reaction was cooled and acidified with 60 ml of 20% HCl, added dropwise. The acidified reaction mixture was refluxed one hour, then concentrated on the rotovap at 40° C. to about 1/3 volume, then diluted with 600 ml water. The mixture was basified, then extracted with CH2Cl2 (2×400 ml). The CH2Cl2 was concentrated to an oil which crystallized when treated with 200 ml ether. The product was filtered off and air dried, giving 8.5 g N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline, m.p. 176°-178° (86%).

1. temperatureAfter 30 min at reflux
2. temperaturethe reaction was cooled
3. additionadded dropwise
4. customThe acidified reaction mixture
5. temperaturewas refluxed one hour
6. concentrationconcentrated on the rotovap at 40° C. to about 1/3 volume
7. additiondiluted with 600 ml water
8. extractionextracted with CH2Cl2 (2×400 ml)
9. concentrationThe CH2Cl2 was concentrated to an oil which
10. customcrystallized when
11. additiontreated with 200 ml ether
12. filtrationThe product was filtered off
13. customair dried