反应详情

6,7,8-Triacetoxy-1-bromomethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane (as described in Example 1 of the Japanese Patent Application No. 144309/1981, pp. 37) (4.1 g) is dissolved in dimethylformamide (15 ml), and sodium azide (1.0 g) is added to the solution, followed by stirring under heating on a bath of the temperature of 130° to 140° C. for 7 hours. The reaction mixture is concentrated under reduced pressure and further freed of the dimethylformamide azeotropically with toluene, under reduced pressure. 20% Aqueous methanol (100 ml) is added to the residue, which is then allowed to stand overnight in a refrigerator. The resultant crystals are recovered by filtration, washed with 20% aqueous methanol cooled with ice, and dried to produce 6,7,8-triacetoxy-1-azidomethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane (2.7 g).

1. temperatureunder heating on a bath of the temperature of 130° to 140° C. for 7 hours
2. concentrationThe reaction mixture is concentrated under reduced pressure
3. addition20% Aqueous methanol (100 ml) is added to the residue, which
4. filtrationThe resultant crystals are recovered by filtration
5. washwashed with 20% aqueous methanol
6. temperaturecooled with ice
7. customdried