Potassium Iodide → Di-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylate

HRID 36597

반응식

HRID 36597 반응식
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:43]([CH:45]1[O:47][CH2:46]1)Br>CC(CC)=O>[C:1]([O:5][C:6]([N:8]1[CH2:46][CH:45]([OH:47])[CH2:43][N:9]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 85431Di-tert-butyl bicarbamateHCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 10334299Di-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylate

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

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.

후처리

  1. concentrationThe resulting suspension is concentrated
  2. addition500 ml of diethyl ether are added
  3. filtrationthe reaction mixture is then filtered
  4. concentrationthe tiltrate is concentrated
  5. customPurification of the crude product by means of column chromatography

출처 및 근거

ORD 기록
ord-da71adb801284935aabd431835879a32
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416065

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