Methyl 2-(4-benzyl-1-(4-methyl-2-nitrophenyl)piperazin-2-yl)acetate → 3-Benzyl-9-methyl-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

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Reaction Conditions

Reaction Steps

To a solution of Example 49A (150 mg, 0.392 mmol) in acetic acid (5 mL) was added iron powder (65.5 mg, 1.17 mmol), and the reaction was heated to 80° C. for 14 hours. The solution was then concentrated onto silica gel and purified via flash chromatography (0-30% methanol/dichloromethane). The pure fractions were partitioned between dichloromethane and 1M NaOH. The organic layer was collected and dried with MgSO4 to afford title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.41 (s, 1H), 7.20-7.41 (m, 5H) 6.86-7.01 (m, 2H), 6.73 (s, 1H), 3.53 (s, 2H), 3.02-3.27 (m, 2H), 2.67-3.00 (m, 3H), 2.42-2.48 (m, 1H) 2.04-2.30 (m, 5H) 1.84 (d, J=13.22 Hz, 1H); MS (APCI+) m/z 322 (M+H)+.

Provenance & Evidence