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

HRID 70791
ノート
印刷プレビュー

反応式

HRID 70791 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8e4cd38ad5d341e59ca3b59df05cafe4
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822688B2

反応ノート

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