(3aR,8aS)-5-Nitro-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one → (3aR,8aS)-5-amino-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one

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Reaction Steps

(3aR,8aS)-5-Nitro-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one (1.3 g, 5.45 mmol) was dissolved in EtOH (50 mL), transferred to par hydrogenation flask. Pd/C (450 mg) transferred to above flask and subjected to hydrogenation at 30 PSI for 2 h. Reaction mixture filtered through Celite and washed the filter cake with EtOH. Filtrate was concentrated and purified by silica gel column chromatography (50-100% EtOAc:hexanes) to provide (3aR,8aS)-5-amino-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one (720 mg, 69%) as a white solid. 1H NMR (DMSO-d6): δ 8.23 (s, 1H), 6.90 (d, 1H, J=8.2 Hz), 6.52-4.49 (m, 2H), 5.20 (app t, 1H, J=6.1 and 7.0 Hz), 5.04 (br s, 2H), 4.91 (d, 1H, J=7.0 Hz), 3.13 (dd, 1H, J=6.7 and 17.0 Hz), 2.89 (d, 1H, J=17.0 Hz). LCMS: purity: 99%; MS (m/e): 191 (MH+).

Provenance & Evidence