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

HRID 1793807노트

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HRID 1793807 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22219611HCID 22219611, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-18de1c8ffdbb4e7fab89bbefe2407c34
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022694B2

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