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

HRID 1394440ノート

反応式

HRID 1394440 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-103677e0a53844c2b2bcdfa3e37ad66a
出典データセット
uspto-grants-2008_03
特許番号
US07348337B2

反応ノート

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