反应详情

温度

-78 °C

(1R*,2R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 14; 10.72 g, 23.77 mmol) was dissolved in THF (200 ml) then cooled to −78° C. and lithium naphthalenide added until a permanent green colour was observed. Each portion was then quenched with saturated ammonium chloride solution then extracted with ethyl acetate (×3) and the extracts dried (MgSO4) and concentrated in vacuo. The extracts were combined to give a yellow oil/solid. This was purified by flash column chromatography [20%-40% ethyl acetate in iso-hexane] to give a yellow solid which was repurified by flash column chromatography [25% ethyl acetate in iso-hexane] to give the title compound as a clear yellow oil (5.37 g, 73%).

1. customEach portion was then quenched with saturated ammonium chloride solution
2. extractionthen extracted with ethyl acetate (×3)
3. dry with materialthe extracts dried (MgSO4)
4. concentrationconcentrated in vacuo
5. customto give a yellow oil/solid
6. customThis was purified by flash column chromatography [20%-40% ethyl acetate in iso-hexane]
7. customto give a yellow solid which
8. customwas repurified by flash column chromatography [25% ethyl acetate in iso-hexane]