Cyanogen Bromide → HCID 53643109、化合物

HRID 1885736ノート

反応式

HRID 1885736 の反応式
[N:1]#[C:2]Br.[Cl:4][C:5]1[CH2:6][N:7]=[CH:8][C:9]2([CH3:23])[CH:20]([CH3:21])[CH:18]3[CH2:19][C:13]4=[C:14]([N:17]3C)[CH2:15][CH2:16][C:10]2=[C:11]4[CH:12]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:4][C:5]1[CH2:6][N:7]=[CH:8][C:9]2([CH3:23])[CH:20]([CH3:21])[CH:18]3[CH2:19][C:13]4=[C:14]([N:17]3[C:2]#[N:1])[CH2:15][CH2:16][C:10]2=[C:11]4[CH:12]=1

参加物

5

反応物 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 53780973HCID 53780973、化合物

生成物 1

HCID 53643109HCID 53643109、化合物収率 162.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To a stirred solution of 1.68 g of cyanogen bromide and 35 ml of chloroform was added, at room temperature with stirring under nitrogen, a solution of 3.8 g of 10-chloro-1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 100 ml of chloroform. The mixture was heated at reflux for 2 hr, under nitrogen, and cooled to room temperature. Dilute aqueous sodium bicarbonate solution was added and the layers separated. The organic layer was extracted with dilute aqueous sodium bicarbonate solution. The combined aqueous layers were extracted with ether and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 6.41 g (78%) of 10-chloro-3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo-[3,2-h][3]benzazocine.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hr, under nitrogen
  3. customthe layers separated
  4. extractionThe organic layer was extracted with dilute aqueous sodium bicarbonate solution
  5. extractionThe combined aqueous layers were extracted with ether
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customthe residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate)

出典と根拠

ORDレコード
ord-a6da75b1cfa644238fa5f2ef19f01833
出典データセット
uspto-grants-1992_09
特許番号
US05145965

反応ノート

読み込み中…