反应详情

To a solution of (1S,4S,7S)-7-{[9-(tert-butyldimethylsilanyloxy)nonyl]methylamino}-bicyclo[2.2.1]heptan-2-one (4.11 g, 10.4 mmol max) in dry THF (41 mL) at −5° C. under a nitrogen atmosphere was added lithium tri-tert-butoxyaluminum hydride (3.44 g, 13.5 mmol). After 1.5 h at −5° C. more lithium tri-tert-butoxyaluminum hydride (2.64 g, 10.4 mmol) was added. After 1 h at −5° C. the reaction was quenched with satd ammonium chloride solution (aq) and partitioned between ethyl acetate and water. The solids were removed by filtration and washed with ethyl acetate. The phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with satd NaHCO3 (aq), brine, dried (Na2SO4), filtered, and concentrated to dryness to afford a turbid yellow oil. The crude product was purified by column chromatography over silica gel using a gradient of 7.5-10% MeOH/DCM as eluent. After evaporation of the volatiles a light yellow/brown viscous oil was obtained.

1. customAfter 1 h at −5° C. the reaction was quenched with satd ammonium chloride solution (aq)
2. custompartitioned between ethyl acetate and water
3. customThe solids were removed by filtration
4. washwashed with ethyl acetate
5. customThe phases were separated
6. extractionthe aqueous layer was extracted with ethyl acetate
7. washThe combined organic layers were washed with satd NaHCO3 (aq), brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated to dryness
11. customto afford a turbid yellow oil
12. customThe crude product was purified by column chromatography over silica gel using a gradient of 7.5-10% MeOH/DCM as eluent
13. customAfter evaporation of the volatiles a light yellow/brown viscous oil
14. customwas obtained