反応 #84701

反応方程式

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

ammonium chloride

sodium azide

→

ethyl 3-azido-4-hydroxycyclohexanecarboxylate

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   ろ過After any insoluble matter was collected by filtration
2. 2
   濃縮the filtrate was concentrated under reduced pressure while not
3. 3
   その他to evaporate to dryness
4. 4
   ろ過collected by the previous filtration
5. 5
   workup.DISSOLUTIONthe thus-obtained mixture was dissolved in water (500 mL)
6. 6
   抽出The solution was extracted with ethyl acetate (500 mL)
7. 7
   洗浄The extract was washed with water (500 mL×5) and saturated brine
8. 8
   乾燥dried over anhydrous sodium sulfate
9. 9
   ろ過filtered
10. 10
    濃縮concentrated
11. 11
    その他to afford the tile compound (28 g, crude) as an yellow oil

実験手順

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]+.

出典