Ethanol → HCID 67759045、化合物

HRID 356107

反応式

HRID 356107 の反応式
[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[C:4](=O)[CH2:3][CH2:2]2.C1(C)C=CC(S([CH2:20][N+:21]#[C-])(=O)=O)=CC=1.C(O)C.CC(C)([O-])C.[K+]>C(COC)OC>[N:1]12[CH2:9][C@H:5]([CH2:6][CH2:7][CH2:8]1)[C@H:4]([C:20]#[N:21])[CH2:3][CH2:2]2

参加物

6

反応物 4

HCID 702EthanolHCID 161915Tosylmethyl isocyanideHCID 4178971-Azabicyclo(3.3.1)nonan-4-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 67759045HCID 67759045、化合物収率 46.8%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
5 °C

実験手順

To a solution of 2.00 g of 1-azabicyclo[3.3.1]nonan-4-one in 100 ml of dimethoxyethane, 3.65 g of p-toluenesulfonylmethylisocyanide and 1.13 g of ethanol were added, followed by cooling to 5° C. Then, 4.00 g of potassium tert-butoxide was added while keeping the internal temperature below 10° C. The mixture was stirred at room temperature for 30 minutes, followed by further stirring at 40° C. for 30 minutes. The precipitate thus formed was removed by filtration. The residue obtained by evaporation of the solvent was purified by an alumina column chromatography (eluent: chloroform:hexane=1:1). The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1), whereby 1.01 g of (4R*,5R*)-1-azabicyclo[3.3.1]nonane-4-carbonitrile was obtained.

後処理

  1. customthe internal temperature below 10° C
  2. stirringby further stirring at 40° C. for 30 minutes
  3. customThe precipitate thus formed
  4. customwas removed by filtration
  5. customThe residue obtained by evaporation of the solvent
  6. customwas purified by an alumina column chromatography (eluent: chloroform:hexane=1:1)
  7. customThe resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-2e57fe313bf04f39bdf3ad8a3c083277
出典データセット
uspto-grants-1998_11
特許番号
US05834499

関連ノート

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