1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86621468、化合物

HRID 1711593ノート

反応式

HRID 1711593 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2N)=[CH:5][CH:4]=1.[N:13]12CCCN=C1CCCCC2.[CH:24]([S:27](Cl)(=[O:29])=[O:28])([CH3:26])[CH3:25]>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH:10]2[CH2:25][CH:24]([S:27]([NH2:13])(=[O:29])=[O:28])[CH3:26])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 67320767Cyclopropanamine, 2-(4-chlorophenyl)-, hydrochloride (1:1), (1R,2S)-rel-

生成物 1

HCID 86621468HCID 86621468、化合物収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trans-2-(4-chlorophenyl)cyclopropanamine hydrochloride (see Bioorganic and Medical Chemistry 12(9), 2021-2034, 2004) (628 mg, 3.08 mmol) was suspended in dry dichloromethane (15 ml) and cooled to 0° C. with stirring under argon. 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.40 g, 9.225 mmol) was added, followed by the dropwise addition of isopropylsulfonyl chloride (877 mg, 6.15 mmol) with stirring under an atmosphere of argon. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was then washed with 1 N HCl (2×50 ml). The organic layer was dried over sodium sulphate and evaporated in vacuo to give a yellow oil. The crude product was chromatographed on a 5 g isolute silica Sep-Pak® column eluting from 0-50% ethyl acetate in petroleum ether to give the title compound (570 mg, 68%); mass spectrum (API−): Found 272 (MH−);

後処理

  1. stirringwith stirring under an atmosphere of argon
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. washThe reaction mixture was then washed with 1 N HCl (2×50 ml)
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customevaporated in vacuo
  7. customto give a yellow oil
  8. customThe crude product was chromatographed on a 5 g isolute silica Sep-Pak® column
  9. washeluting from 0-50% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-47ad073884744b4bb5c0b194344655c8
出典データセット
uspto-grants-2010_09
特許番号
US07790758B2

反応ノート

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