1263774-42-0

75-87-6

344-25-2

1263774-42-0

General procedure for the synthesis of (7AR)-3-(trichloromethyl)tetrahydropyrrolo[1,2-C]azol-1(3H)-one from trichloroacetaldehyde and D-proline: trichloroacetaldehyde (0.68 mL, 6.94 mmol) was added to a solution of D-proline (0.4 g, 3.48 mmol) in acetonitrile (8 mL), and the reaction mixture was stirred for 8 hours at room temperature. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was ground with ether. After filtration and drying, 0.23 g (7AR)-3-(trichloromethyl)tetrahydropyrrolo[1,2-C]azol-1(3H)-one (D48) was obtained. Mass spectrum (electrospray positive ion mode) m/z: 244.0 [MH+], calculated value C7H8Cl3NO2 requires 242.96. 1H NMR (400 MHz, CDCl3) δ (ppm): 4.15 (dd, J = 4.5, 8.6 Hz, 1H), 3.52-3.36 (m, J = 7.0, 7.0, 10.5 Hz, 1H) ), 3.22-3.07 (m, 1H), 2.33-2.20 (m, 1H), 2.19-2.08 (m, 1H), 1.96 (quintet, J = 5.9, 12.1 Hz, 1H), 1.84-1.69 (m, 1H), 1.61 (br.s., 1H).