Reacción #327626

Ecuación de reacción

(7R,8aS)-2-[(3-tert-Butylphenyl)sulfonyl]-7-{[5-(prop-1-en-2-yl)pyrazin-2-yl]oxy}octahydropyrrolo[1,2-a]pyrazine

(7R,8aS)-2-[(3-tert-butylphenyl)sulfonyl]-7-{[5-(prop-1-en-2-yl)pyrazin-2-yl]oxy}octahydropyrrolo[1,2-a]pyrazine

hydrogen

→

title compound

Rendimiento 56.0%

(7R,8aS)-2-[(3-tert-butylphenyl)sulfonyl]-7-[(5-isopropylpyrazin-2-yl)-oxy]octahydropyrrolo[1,2-a]pyrazine

Rendimiento 56.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered through a polypropylene membrane
2. 2
   Concentraciónthe filtrate was concentrated
3. 3
   Otrothe residue was purified by column chromatography on silica gel
4. 4
   Lavadoeluted with ethyl acetate/hexane (3:7)

Procedimiento

(7R,8aS)-2-[(3-tert-Butylphenyl)sulfonyl]-7-{[5-(prop-1-en-2-yl)pyrazin-2-yl]oxy}octahydropyrrolo[1,2-a]pyrazine (164.3 mg, 0.360 mmol, Example 113) in ethanol (5 mL) was added to Raney® nickel 2800 water slurry (202.9 mg, 1.556 mmol) in a 20 mL pressure bottle. The mixture was stirred under 30 psi of hydrogen at ambient temperature for 15 hours. The mixture was filtered through a polypropylene membrane, the filtrate was concentrated, and the residue was purified by column chromatography on silica gel eluted with ethyl acetate/hexane (3:7) to give the title compound (56% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (m, 6H), 1.33 (s, 9H), 1.62 (m, 1H), 1.94 (m, 2H), 2.26 (m, 4H), 2.99 (m, 2H), 3.54 (m, 1H), 3.62 (m, 1H), 3.79 (m, 1H), 5.20 (m, 1H), 7.59 (m, 2H), 7.67 (m, 1H), 7.78 (s, 1H), 8.06 (m, 1H), 8.20 (m, 1H); MS (ESI) m/z 459 (M+H)+.

Fuente