反应详情

To a stirred solution of 4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile (3.5 g, 11 mmol) in THF (35 ml) at 0° C. was added dropwise lithium aluminium hydride (1M solution in ether, 44 ml, 44 mmol). The reaction was allowed to warm up to room temperature and stirred for 4 hours until complete. The reaction mixture was cooled to 0° C., water (1.66 mL) was added followed by NaOH (2.0M, 1.66 mL) and water (4.97 mL). The mixture was filtered through a short pad of celite, eluting with dichloromethane:methanol (97:3, 150 ml) and concentrated in vacuo. Solid obtained was partitioned between ethyl acetate (50 ml) and sodium bicarbonate (50 ml). The organic layer was then dried over sodium sulphate, filtered and concentrated in vacuo to give the title compound (2.04 g, 58%). LRMS APCI+ m/z 322 [MH]+.

1. temperatureThe reaction mixture was cooled to 0° C.
2. filtrationThe mixture was filtered through a short pad of celite
3. washeluting with dichloromethane:methanol (97:3, 150 ml)
4. concentrationconcentrated in vacuo
5. customSolid obtained
6. customwas partitioned between ethyl acetate (50 ml) and sodium bicarbonate (50 ml)
7. dry with materialThe organic layer was then dried over sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated in vacuo