تفاعل #84701

معادلة التفاعل

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

ammonium chloride

sodium azide

→

ethyl 3-azido-4-hydroxycyclohexanecarboxylate

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   ترشيحAfter any insoluble matter was collected by filtration
2. 2
   تركيزthe filtrate was concentrated under reduced pressure while not
3. 3
   أخرىto evaporate to dryness
4. 4
   ترشيحcollected by the previous filtration
5. 5
   workup.DISSOLUTIONthe thus-obtained mixture was dissolved in water (500 mL)
6. 6
   استخلاصThe solution was extracted with ethyl acetate (500 mL)
7. 7
   غسيلThe extract was washed with water (500 mL×5) and saturated brine
8. 8
   تجفيفdried over anhydrous sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated
11. 11
    أخرىto afford the tile compound (28 g, crude) as an yellow oil

الإجراء التجريبي

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]+.

المصدر