Methanol → 5,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

HRID 2255948ノート

反応式

HRID 2255948 の反応式
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=O)[NH:5][C:4]=2[CH:3]=[CH:2]1.B.CSC.CO>O1CCCC1>[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1

参加物

5

反応物 3

HCID 887MethanolHCID 8707434H,5H,6H,7H,8H-thieno[3,2-b]azepin-5-oneHCID 12423031(Dimethyl sulfide)trihydroboron

生成物 1

HCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine収率 79.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of 21.2 g of 5,6,7,8-tetrahydro-4H-thieno[3 2-b]azepin-5-one in 100 ml of tetrahydrofuran under argon, chilled to 0° C. is added 25.2 ml of a 10.0 molar solution of borane-dimethylsulfide in tetrahydrofuran. The solution is stirred at room temperature for 16 hours and is refluxed for 5 hours. The mixture is cooled to room temperature and 85 ml of methanol added dropwise (exotherm). The solvent is removed and 100 ml of methanol is added (2 times) and after each addition the solvent is removed. To the residual solid (dried under vacuum) is added 126 ml of 2N NaOH and the mixture refluxed 3 hours. The mixture is chilled (2 hours) and extracted with dichloromethane. The extract is dried (Na2SO4) and the solvent removed to give 15.4 g of brown solid, m.p. 55°-57° C. A sample (3 g) is sublimed to give 2.6 g of crystals, m.p. 64°-65° C.

後処理

  1. temperatureis refluxed for 5 hours
  2. temperatureThe mixture is cooled to room temperature
  3. customThe solvent is removed
  4. addition100 ml of methanol is added (2 times)
  5. additionafter each addition the solvent
  6. customis removed
  7. customTo the residual solid (dried under vacuum)
  8. additionis added 126 ml of 2N NaOH
  9. temperaturethe mixture refluxed 3 hours
  10. temperatureThe mixture is chilled (2 hours)
  11. extractionextracted with dichloromethane
  12. dry with materialThe extract is dried (Na2SO4)
  13. customthe solvent removed

出典と根拠

ORDレコード
ord-151df3ab53da414e96e3983949baa404
出典データセット
uspto-grants-1997_08
特許番号
US05654297

反応ノート

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