反应详情

(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+).

1. customtransferred to par hydrogenation flask
2. customReaction mixture
3. filtrationfiltered through Celite
4. washwashed the filter cake with EtOH
5. concentrationFiltrate was concentrated
6. custompurified by silica gel column chromatography (50-100% EtOAc:hexanes)