反应详情

To a solution of 4a-methyl-6-(phenylsulfanyl)-1,2,3,4,4a,9a-hexahydro[1]benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (0.327 g, 0.82 mmol) in methanol (10 mL, 0.2 mol) was added water (0.5 mL, 0.03 mol) and Oxone® (2.0 g, 0.0032 mol). The reaction was stirred overnight at room temperature. The reaction mixture was filtered and the filtrate concentrated. The residue was dissolved in DCM and washed with brine, dried, filtered and concentrated. The crude product was purified on a 12 g silica gel column eluting with hexanes to 2:1 hexanes:ethyl acetate and then stirred in 4 M HCl in dioxane (5 mL, 0.04 mol) for 30 min. The product was precipitated by addition of DCM and ether. The solid was filtered, washed with ether and dried under house vacuum to afford the title compound. mp 236-238° C. dec.; MS m/z 330 [M+H]+. 1H-NMR (400 MHz, DMSO): δ 1.45 (s, 3H), 1.75 (m, 1H), 1.90 (m, 1H), 2.82 (m, 1H), 3.03 (m, 1H), 3.35-3.56 (m, 2H), 4.63 (s, 1H), 7.08 (d, J=8.9 Hz, 1H), 7.58-7.70 (m, 3H), 7.81 (d, J=8.85 Hz, 1H), 7.91-7.96 (m, 3H), 8.91 (bs, 1H), 9.91 (bs, 1H).

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate concentrated
3. dissolutionThe residue was dissolved in DCM
4. washwashed with brine
5. customdried
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified on a 12 g silica gel column
9. washeluting with hexanes to 2:1 hexanes
10. customThe product was precipitated by addition of DCM and ether
11. filtrationThe solid was filtered
12. washwashed with ether
13. customdried under house vacuum