تفاعل #633635

معادلة التفاعل

Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate

ammonium chloride

sodium azide

→

title compound

المردود 92.7%

Ethyl (1R*,3S*,4S*)-3-azido-4-hydroxycyclohexane-1-carboxylate

المردود 92.7%

المذيبات

N,N-dimethyl-formamide

ظروف التفاعل

المعالجة

1. 1
   تركيزThe solvent was concentrated to about 1/3
2. 2
   workup.ADDITIONthe residue was diluted with water and ethyl acetate
3. 3
   workup.STIRRINGto conduct stirring for 3 minutes
4. 4
   غسيلThe resultant organic layer was washed with water and saturated saline
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   أخرىthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

الإجراء التجريبي

Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil.

المصدر