反应 #66065

反应方程式

product

7-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

→

title compound

7-[2-(6-methylpyridin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

溶剂

ethanol

反应条件

后处理

1. 1
   其他The reaction flask was evacuated
2. 2
   其他purged with nitrogen (3 cycles)
3. 3
   其他then evacuated
4. 4
   其他purged with hydrogen (4 cycles)
5. 5
   其他The flask was evacuated
6. 6
   其他purged with nitrogen (3 cycles)
7. 7
   过滤the reaction mixture was filtered
8. 8
   浓缩The filtrate was concentrated under vacuum
9. 9
   其他the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 35-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

实验过程

Adam's catalyst (PtO2, 7 mg, 0.031 mmol; Aldrich) was added to a solution of the product of Example 1D (60 mg, 0.18 mmol) in ethanol (5 mL). The reaction flask was evacuated and purged with nitrogen (3 cycles) then evacuated and purged with hydrogen (4 cycles), and the mixture was stirred under hydrogen (1 atm) at room temperature for 18 hours. The flask was evacuated and purged with nitrogen (3 cycles), and the reaction mixture was filtered. The filtrate was concentrated under vacuum, and the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 35-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.06 (td, J=7.3, 3.7 Hz, 4 H), 2.45 (s, 3 H), 2.99 (t, J=7.6 Hz, 2 H), 3.01-3.09 (m, 3 H), 3.11 (t, J=7.6 Hz, 2 H), 3.23 (dq, J=7.3, 7.1 Hz, 2 H), 4.20 (s, 2 H), 6.77 (d, J=7.0 Hz, 1 H), 6.88 (t, J=7.5 Hz, 1 H), 7.13 (d, J=7.6 Hz, 1 H), 7.14 (d, J=7.9 Hz, 1 H), 7.49 (dd, J=7.9, 2.1 Hz, 1 H), 8.11 (d, J=1.8 Hz, 1 H); MS (APCI) m/z 332 (M+H)+.

来源