Hydrazinecarboxaldehyde → 4-(1-Phenyl-1-(2-formylhydrazinocarbonyl)-methylene)piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1394440노트

반응식

HRID 1394440 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](O)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:45]([NH:47][NH2:48])=[O:46]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]([NH:48][NH:47][CH:45]=[O:46])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 12229HydrazinecarboxaldehydeHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 670464544-(1-Phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 670463754-(1-Phenyl-1-(2-formylhydrazinocarbonyl)-methylene)piperidine-1-carboxylic Acid Tert-Butyl Ester수율 124.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(1-phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester (1.05 g, 3.31 mmol), EDCI (0.888 g, 4.63 mmol) and HOBt (0.626 g, 4.63 mmol) in DMF (4 mL) was stirred for 30 min at room temperature and then formic hydrazide (3.97 g, 66.2 mmol) was added. Stirring was continued for 1 h and then the mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed (H2O ×3, brine), dried (Na2SO4) and evaporated to give the title compound (1.48 g, 97%) as a colorless oil:

후처리

  1. stirringStirring
  2. waitwas continued for 1 h
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed (H2O ×3, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-103677e0a53844c2b2bcdfa3e37ad66a
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348337B2

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