1,1'-Carbonyldiimidazole → 3,4-Dimethoxyphenethyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

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Reaction Steps

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.

Provenance & Evidence