반응 #2036623

반응 방정식

4-cyano-piperidine-1-carboxylic acid benzyl ester

sodium azide

→

4-(1H-Tetrazol-5-yl)-piperidine-1-carboxylic acid benzyl ester

수율 132.3%

용매

2-propanol

water

ethyl acetate

반응 조건

후처리

1. 1
   기타The reaction mixture was then partitioned between aqueous 3.0N HCl (1.5 mL) and ethyl acetate
2. 2
   workup.STIRRINGstirred vigorously until 2 clear phases
3. 3
   기타were obtained
4. 4
   추출Aqueous layer was then extracted with ethyl acetate and combined ethyl acetate layers
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   기타the solvent evaporated in vacuo
8. 8
   기타to yield a crude residue
9. 9
   세척washed with 0.25N aqueous sodium hydroxide
10. 10
    추출extracted with ethyl acetate
11. 11
    건조Ethyl acetate layer was dried over Na2SO4
12. 12
    여과filtered
13. 13
    기타the solvent evaporated in vacuo
14. 14
    기타to yield a crude gum
15. 15
    기타The gum was purified via flash chromatography (4% methanol in dichloromethane)

실험 절차

A mixture of 4-cyano-piperidine-1-carboxylic acid benzyl ester (0.73 g, 3.0 mmol), sodium azide (0.39 g, 6.0 mmol) and zinc bromide (0.33 g, 1.5 mmol) in 2-propanol (5 mL) and water (10 mL) was stirred at 120° C. for 3 days into a pressure tube. The reaction mixture was then partitioned between aqueous 3.0N HCl (1.5 mL) and ethyl acetate and then stirred vigorously until 2 clear phases were obtained. Aqueous layer was then extracted with ethyl acetate and combined ethyl acetate layers dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude residue. The residue was dissolved in ethyl acetate (10 mL) and washed with 0.25N aqueous sodium hydroxide. Aqueous layer was acidified to pH=1 with aqueous 3.0N HCl and extracted with ethyl acetate. Ethyl acetate layer was dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude gum. The gum was purified via flash chromatography (4% methanol in dichloromethane) to yield 4-(1H-Tetrazol-5-yl)-piperidine-1-carboxylic acid benzyl ester as a gum (1.14 g, 66%).

출처