反应详情

To a suspension of 7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetic acid in anhydrous THF (20 ml) at 0° C. was added 1.0M borane in THF (25 ml). The reaction mixture was slowly warmed to ambient temperature and stirring was continued for 4 h. Since the reaction was not proceeding to completion, additional borane (10 ml) was added and the solution heated at reflux for 1 h. Upon cooling to ambient temperature, the reaction was quenched by the addition of methanol (1 ml) and 6M hydrochloric acid (5 ml). The solution was heated at reflux for 2 h to decompose any borate intermediates and the solvent concentrated at the rotoevaporator. The resulting oil was taken up in water, made basic with dilute NaOH, and extracted twice with dichloromethane. The dried (MgSO4) organic extracts were concentrated to give a solid. This solid was dissolved in hot ethanol (75 ml) and hydrochloric acid in ethanol added to give an acidic solution. The product was isolated by filtration of the precipitate to give the title compound as a light yellow solid (2.28 g, 84%), m.p. 238-40° C.

1. additionwas added
2. temperaturethe solution heated
3. temperatureat reflux for 1 h
4. temperatureUpon cooling to ambient temperature
5. customthe reaction was quenched by the addition of methanol (1 ml) and 6M hydrochloric acid (5 ml)
6. temperatureThe solution was heated
7. temperatureat reflux for 2 h
8. concentrationthe solvent concentrated at the rotoevaporator
9. extractionextracted twice with dichloromethane
10. dry with materialThe dried (MgSO4) organic extracts
11. concentrationwere concentrated
12. customto give a solid
13. customto give an acidic solution
14. customThe product was isolated by filtration of the precipitate