Reaktion #962444

Reaktionsgleichung

Sodium azide

compound

((5aR,9bS)-3,3a-Dihydroxy-5a,9-dimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydronaphtho[1,2-b]furan-3-yl)methyl 4-methylbenzenesulfonate

→

title compound

(5aR,9bS)-3-(Azidomethyl)-3,3a-dihydroxy-5a,9-dimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   Sonstigedried
3. 3
   workup.DISSOLUTIONwas dissolved in water (25 mL)
4. 4
   Extraktionwas extracted with ethyl acetate (3×50 mL)
5. 5
   WaschenThe ethyl acetate layer was washed with water and brine
6. 6
   Trocknenwas dried over sodium sulfate
7. 7
   SonstigeSolvent was removed
8. 8
   Waschencrude product was washed with petroleum ether

Vorschrift

Sodium azide (32.5 mg, 0.5 mmol) was added to the solution of compound of example 5 (218 mg, 0.5 mmol) in dimethylformamide (DMF) (2 mL) and stirred at 50° C. under nitrogen atmosphere for 24 hours. The reaction mixture was concentrated, dried and was dissolved in water (25 mL) and was extracted with ethyl acetate (3×50 mL). The ethyl acetate layer was washed with water and brine and was dried over sodium sulfate. Solvent was removed and crude product was washed with petroleum ether, to obtain the title compound.

Quelle