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Benzyl chloroformate → 2-Benzyl 7-(tert-butyl) 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate

HRID 70791
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HRID 70791 반응식
[OH-].[Na+].Cl[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:14]([C:16]1([CH2:29]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)#[N:15]>O1CCOCC1>[CH2:29]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:14][N:15]1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 866770551,1-Dimethylethyl 4-cyano-4-((((4-methylphenyl)sulfonyl)oxy)methyl)-1-piperidinecarboxylate

생성물 1

HCID 712686312-Benzyl 7-(tert-butyl) 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate수율 85.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Under ice-cooling, 1M sodium hydroxide aqueous solution (6.0 ml) and benzyl chloroformate (1.03 g) were sequentially added to a dioxane (50 ml) suspension of tert-butyl 4-cyano-4-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate (2.15 g), and stirring was performed at room temperature for 16 hours. The reaction liquid was concentrated under reduced pressure, and extracted with EtOAc. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain 2-benzyl 7-tert-butyl 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate (1.68 g).

후처리

  1. temperatureUnder ice-cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-8e4cd38ad5d341e59ca3b59df05cafe4
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822688B2

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