Potassium Carbonate → tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

HRID 470616ノート

反応式

HRID 470616 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(OP([CH2:29][C:30]#[N:31])(=O)OCC)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:29][C:30]#[N:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate2 回

生成物 1

HCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (compound of Example 13; 13.5 g, 67 mmol), anhydrous potassium carbonate (11.22 g, 81 mmol) and cyanomethyl phosphonic acid diethylester (15.6 g, 88 mmol) in THF (70 mL) was heated at reflux for 12 h. THF was evaporated and the residue was dissolved in chloroform (2×50 mL). The resulting solution was washed with water (2×50 mL) and brine (50 mL). The organic phase obtained was dried over anhydrous sodium sulphate and concentrated to afford the title compound.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. customTHF was evaporated
  4. dissolutionthe residue was dissolved in chloroform (2×50 mL)
  5. washThe resulting solution was washed with water (2×50 mL) and brine (50 mL)
  6. customThe organic phase obtained
  7. dry with materialwas dried over anhydrous sodium sulphate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-395f0cda274f486ebad312f96e2a7d81
出典データセット
uspto-grants-2014_01
特許番号
US08629277B2

反応ノート

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