반응 #64875

반응 방정식

tetrabutylammonium fluoride

hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester

potassium carbonate

epibromohydrin

potassium iodide

→

4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester

용매

ethyl methyl ketone

반응 조건

후처리

1. 1
   농축The resulting suspension is concentrated
2. 2
   workup.ADDITION500 ml of diethyl ether are added
3. 3
   여과the reaction mixture is then filtered
4. 4
   농축the tiltrate is concentrated
5. 5
   기타Purification of the crude product by means of column chromatography

실험 절차

46.4 g of hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester, 69.0 g of potassium carbonate, 3.3 g of potassium iodide, 20 ml of tetrabutylammonium fluoride (1 molar solution in tetrahydrofuran) and 21 ml of epibromohydrin are boiled under reflux for 48 hours in 400 ml of ethyl methyl ketone. The resulting suspension is concentrated, and 500 ml of diethyl ether are added thereto; the reaction mixture is then filtered and the tiltrate is concentrated. Purification of the crude product by means of column chromatography yields 27.1 g of the desired 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in the form of white crystals; m.p. 100°-102° C.

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