反应详情

To a solution of t-butyl alcohol (9.1 g, 123 mmol), 50 ml ether, and ammonia (150 mL) is added (S)-2-t-butoxycarbonyl-1,2,3,4-tetrahydro-3-hydroxymethyl-7-hydroxyisoquinoline (5 mmol). The solution is brought to reflux, and lithium shot (0.51 g, 82 mmol) is added over 30 minutes. The solution is allowed to reflux for 3 hours, and solid NH4Cl added until the color disappears. The ammonia is allowed to evaporate overnight, ice-water is added, and the organic layer separated. The aqueous layer is extracted with chloroform and the combined organic phases are washed with brine, dried and evaporated. The crude product is redissolved in methanol, 5% Pt/C added and the solution shaken under 3 atm H2 for 6 hours to complete the reduction. The catalyst is filtered and the solvent evaporated. The resulting residue is purified by silica gel flash column chromatography to give the title compound.

1. temperatureto reflux
2. additionis added over 30 minutes
3. temperatureto reflux for 3 hours
4. customto evaporate overnight
5. additionice-water is added
6. customthe organic layer separated
7. extractionThe aqueous layer is extracted with chloroform
8. washthe combined organic phases are washed with brine
9. customdried
10. customevaporated
11. dissolutionThe crude product is redissolved in methanol
12. addition5% Pt/C added
13. filtrationThe catalyst is filtered
14. customthe solvent evaporated
15. customThe resulting residue is purified by silica gel flash column chromatography