4-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]benzonitrile → 1-{4-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]phenyl}methanamine

Participants

Reaction Steps

The product of Example 68 (676 mg, 3.0 mmole) in 50 mL of 20% ammonia in methanol was stirred in the presence of 6.8 g Raney-Nickel under an atmosphere of hydrogen at 60 psi at room temperature for 4 hours. Catalyst was removed by filtration through CELITE® and the filtrate concentrated under reduced pressure. The resulting oil was purified by flash chromatography (eluting with a mixture of 5% basic methanol in dichloromethane) to provide the titled compound. 1H NMR (CDCl3) δ ppm 7.17 (d, J=8.82 Hz, 2H) 6.55 (d, J=8.48 Hz, 2H) 4.07-4.16 (m, 1H) 3.77 (s, 2H) 3.45-3.59 (m, 1H) 3.16-3.28 (m, 1H) 2.88-3.04 (m, 1H) 2.63-2.74 (m, 2H) 2.53-2.63 (m, 2H) 2.34 (s, 3H) 2.08-2.23 (m, 1H) 1.86-2.05 (m, 1H); MS (M+H)+=232.

Provenance & Evidence