反应详情

(1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one (Description 3; 3.05 g, 7.03 mmol) was dissolved in hot THF (10 ml) and methanol (150 ml) was added. The mixture was heated at reflux for 2 minutes and cooled to +5° C. Sodium borohydride (600 mg, 15.8 mmol) was added. The reaction mixture was stirred for 20 minutes at +5° C. The cooling bath was removed and the mixture was stirred for 90 minutes at ambient temperature. Saturated aqueous NaHCO3 (10 ml) was added and the mixture was concentrated in vacuo. The residue was treated with water and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The solid residue was crystallised from acetone:iso-hexane to give the title compound (2.95 g, 97%) as white crystals.

1. temperatureThe mixture was heated
2. temperatureat reflux for 2 minutes
3. temperaturecooled to +5° C
4. customThe cooling bath was removed
5. stirringthe mixture was stirred for 90 minutes at ambient temperature
6. additionSaturated aqueous NaHCO3 (10 ml) was added
7. concentrationthe mixture was concentrated in vacuo
8. additionThe residue was treated with water
9. extractionextracted with ethyl acetate (3×50 ml)
10. dry with materialThe combined organic extracts were dried (Na2SO4)
11. concentrationconcentrated
12. customThe solid residue was crystallised from acetone