反应 #1880989

反应方程式

NaOH

Water

water

methyl 6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate

LiAlH4

→

title product

收率 31.4%

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

收率 31.4%

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture was stirred for 30 min
2. 2
   workup.ADDITIONcelite was added
3. 3
   过滤the mixture was filtered through celite
4. 4
   浓缩the filtrate concentrated
5. 5
   其他to give 84 mg (98%) of crude product
6. 6
   其他Crystallization from EtOAc/hexane

实验过程

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.

来源