反应详情

(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 9; 151 mg, 0.52 mmol) was treated with sodium hydride (41 mg, 60% in oil, 1.03 mmol) at 0° C. in a solution of THF (2 ml) and allowed to warm to room temperature. The mixture was recooled to 0° C. and 2,5-bis(trifluoromethyl)benzyl bromide (0.24 ml, 1.30 mmol) added and the mixture heated to 50° C. for 2 days. A further 1.30 mmol of the benzyl bromide was added and the mixture further heated for 50° C. for 2 days. The reaction mixture was poured into water and extracted with ethyl acetate (×3), dried (MgSO4) and concentrated in vacuo to give a yellow solid. This was purified by flash column chromatography [25% ethyl acetate in iso-hexane] to give the title compound.

1. customwas recooled to 0° C.
2. temperaturethe mixture heated to 50° C. for 2 days
3. temperaturethe mixture further heated for 50° C. for 2 days
4. extractionextracted with ethyl acetate (×3)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customto give a yellow solid
8. customThis was purified by flash column chromatography [25% ethyl acetate in iso-hexane]