Reaktion #66065

Reaktionsgleichung

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction flask was evacuated
2. 2
   Sonstigepurged with nitrogen (3 cycles)
3. 3
   Sonstigethen evacuated
4. 4
   Sonstigepurged with hydrogen (4 cycles)
5. 5
   SonstigeThe flask was evacuated
6. 6
   Sonstigepurged with nitrogen (3 cycles)
7. 7
   Filtrationthe reaction mixture was filtered
8. 8
   EinengenThe filtrate was concentrated under vacuum
9. 9
   Sonstigethe 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)]

Vorschrift

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)+.

Quelle