Water → 8-Methyl-1,6,7,8,9,10-hexahydroazepino [4,5-g]indole

HRID 1793807ノート

反応式

HRID 1793807 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]3[CH2:20][CH2:19][N:18]([C:21](OC)=O)[CH2:17][CH2:16][C:14]3=2)[CH:9]=[CH:8]1.O.[OH-].[Na+]>C1COCC1>[CH3:21][N:18]1[CH2:17][CH2:16][C:14]2[C:13](=[CH:12][CH:11]=[C:10]3[C:15]=2[NH:7][CH:8]=[CH:9]3)[CH2:20][CH2:19]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22219611HCID 22219611、化合物

生成物 1

HCID 98370848-Methyl-1,6,7,8,9,10-hexahydroazepino [4,5-g]indole収率 31.4%

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

Under N2, a flame-dried, 50-mL, two-necked flask was charged with LiAlH4 (0.10 g, equivalent by weight) and THF (3.0 mL) and cooled to 0° C. A solution of methyl 6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate (0.105 g, 0.43 mmol) in THF (2.0 mL) was then added and the mixture was stirred at room temperature for 16 hours. Water (0.1 mL) was added slowly, followed by 15% NaOH (0.1 mL) and then water (0.3 mL). The mixture was stirred for 30 min, celite was added and the mixture was filtered through celite and the filtrate concentrated to give 84 mg (98%) of crude product. Crystallization from EtOAc/hexane affords 27 mg of the title product as a beige solid: mp 150–153° C.; 1H NMR (400 MHz, CDCl3) δ 8.09 (br, 1 H), 7.39 (d, J=8 Hz, 1 H), 7.17 (t, J=3 Hz, 1 H), 6.91 (d, J=8 Hz, 6.53 (dd, J=2, 3 Hz, 1 H), 3.10–3.05 (m, 4 H), 2.67–2.62 (m, 4 H), 2.40 (s, 3 H); 13C NMR (100 MHz, CDCl3) δ 135.5, 135.0, 126.5, 123.8, 123.8, 123.6, 121.9, 118.0, 103.1, 57.7, 56.8, 47.6, 36.2, 29.3; HRMS (FAB) calcd for C13H16N2+H 201.1392. found 201.1390.

後処理

  1. stirringThe mixture was stirred for 30 min
  2. additioncelite was added
  3. filtrationthe mixture was filtered through celite
  4. concentrationthe filtrate concentrated
  5. customto give 84 mg (98%) of crude product
  6. customCrystallization from EtOAc/hexane

出典と根拠

ORDレコード
ord-18de1c8ffdbb4e7fab89bbefe2407c34
出典データセット
uspto-grants-2006_04
特許番号
US07022694B2

反応ノート

読み込み中…