As a common heterocyclic compound, it belong isothiazole compound,(3aS,6S,7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide,94594-90-8,Molecular formula: C10H17NO2S,mainly used in chemical industry, its synthesis route is as follows.,94594-90-8
To a stirred solution of 4-methyl itaconate (1) (864 mg, 6.0 mmol) in dry CH2Cl2 (23 ml) were added 4-(dimethylamino)pyridine (161 mg, 1.3 mmol) and (S)-(?)-2,10-camphorsultam (15) (431 mg, 2.0 mmol). The mixture was cooled to 0 ¡ãC and N,N?-dicyclohexylcarbodiimide (1.36 g, 6.6 mmol) was added. The mixture was stirred at 0 ¡ãC for 1 h under N2 atmosphere. The solution was warmed to room temperature and further stirred overnight. The resulting precipitates of N,N?-dicyclohexylurea were filtered off and the filtrate was washed successively with 5percent aqueous NaHCO3, water, 1 N HCl, water and brine. The organic layer was dried over anhydrous Na2SO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel [ SiO2 51 g; hexane?EtOAc (5:1 then 3:1 v/v)] to afford amide 2 (612 mg, 90percent) as a colourless solid. Mp 86.2 ¡ãC (from diethyl ether); [alpha]D22 ?82.9 (c 1.95, CHCl3); IR (KBr) 3119, 1738, 1674, 1633, 1436, 1328, 1175, 1132, 1114, 1063, 979, 764 cm?1; 1H NMR (600 MHz) delta 6.05 (1H, d, J=1.0 Hz, =CHH), 5.88 (1H, d, J=1.0 Hz, =CHH), 4.06 (1H, dd, J=7.5, 4.9 Hz, NCH), 3.69 (3H, s, OMe), 3.52 (1H, d, J=13.7 Hz, CHHSO2), 3.47 (1H, d, J=16.1 Hz, CHHCO2Me), 3.45 (1H, d, J=13.7 Hz, CHHSO2), 3.25 (1H, d, J=16.1 Hz, CHHCO2Me), 2.05?2.00 (2H, m, CH2), 2.00?1.85 (3H, m, CH, CH2), 1.49?1.29 (2H, m, CH2), 1.22 (3H, s, Me), 1.00 (3H, s, Me); 13C NMR (100 MHz) delta 169.9, 169.0, 135.6, 127.7, 65.4, 53.2, 51.8, 47.8, 47.5, 44.9, 38.0, 32.9, 26.2, 20.9, 19.7; MS (EI+) (m/z) 341 (M+, 1percent), 310 (15), 277 (16), 218 (19), 127 (100), 99 (72), 69 (32), 59 (25); HRMS calcd for C16H24NO5S (MH+) 342.1375, found 342.1396.
With the synthetic route has been constantly updated, we look forward to future research findings about (3aS,6S,7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide,belong isothiazole compound
Reference£º
Article; Kumazaki, Eri; Nagano, Hajime; Tetrahedron; vol. 69; 16; (2013); p. 3486 – 3494;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com