反应详情

3,4-Dimethoxyphenethyl alcohol (3.64 g; 20 mmol) was added to a stirred suspension of 1,1′-carbonyldiimidazole (3.24 g; 20 mmol) in THF (20 mL), and the mixture was refluxed for 12 h. A solution of 3-benzyl-3,7-diazabicyclo[3.3.1]nonane (4.33 g; 20 mmol; see Example E above) in THF (20 mL) was added and the reaction mixture was refluxed overnight. The solvent was removed and the residue dissolved in H2SO4 (2M; 25 mL) and extracted with diethyl ether. NaOH (3.5 mL; 5M) was added and the aqueous phase extracted with DCM. The organic layer was separated, dried and subjected to column chromatography (DCM:MeOH; gradient 0 to 30% MeOH) to give the sub-title compound in a 29% yield.

1. temperaturethe mixture was refluxed for 12 h
2. temperaturethe reaction mixture was refluxed overnight
3. customThe solvent was removed
4. dissolutionthe residue dissolved in H2SO4 (2M; 25 mL)
5. extractionextracted with diethyl ether
6. additionNaOH (3.5 mL; 5M) was added
7. extractionthe aqueous phase extracted with DCM
8. customThe organic layer was separated
9. customdried