Reacción #84701

Ecuación de reacción

ethyl 7-oxa-bicyclo[4.1.0]heptane-3-carboxylate

ammonium chloride

sodium azide

→

ethyl 3-azido-4-hydroxycyclohexanecarboxylate

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónAfter any insoluble matter was collected by filtration
2. 2
   Concentraciónthe filtrate was concentrated under reduced pressure while not
3. 3
   Otroto evaporate to dryness
4. 4
   Filtracióncollected by the previous filtration
5. 5
   workup.DISSOLUTIONthe thus-obtained mixture was dissolved in water (500 mL)
6. 6
   ExtracciónThe solution was extracted with ethyl acetate (500 mL)
7. 7
   LavadoThe extract was washed with water (500 mL×5) and saturated brine
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated
11. 11
    Otroto afford the tile compound (28 g, crude) as an yellow oil

Procedimiento

A mixture of Racemate-ethyl 7-oxa-bicyclo[4.1.0]heptane-3-carboxylate (24.0 g, 140 mmol), ammonium chloride (13.6 g, 210 mmol) and sodium azide (13.7 g, 210 mmol) in N,N-dimethylformamide (120 mL) was stirred at 76° C. for 13 hours. After any insoluble matter was collected by filtration, the filtrate was concentrated under reduced pressure while not allowing the solvent to evaporate to dryness. The residue was combined with the solid matter collected by the previous filtration, and the thus-obtained mixture was dissolved in water (500 mL). The solution was extracted with ethyl acetate (500 mL). The extract was washed with water (500 mL×5) and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the tile compound (28 g, crude) as an yellow oil. MS (ES+) C9H15N3O3 requires: 213, found: 214 [M+H]+, 236 [M+Na]+.

Fuente