反应详情

A mixture of azetidine-3-carboxylic acid (0.015 g, 0.15 mmol), 1-(4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)ethanone (0.050 g, 0.15 mmol), acetic acid (0.013 mL, 0.22 mmol) in methanol (3.0 mL) was stirred at room temperature for 1 h. Sodium triacetoxyborohydride (0.037 g, 0.17 mmol) was added and the mixture was stirred for 1 h at room temperature. Evaporation and purification by flash chromatography (5% AcOH in CHCl3 and MeOH). The resulting solid was suspended in in an aqueous buffered solution (pH 6, phosphate buffer) and sonicated. The solids were collected by filtration, washed with water and Et2O to give title compound [hS1P1 EC50=313 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (t, J=7.9 Hz, 1H), 7.51-7.59 (m, 2H), 7.14-7.34 (m, 9H), 4.04 (s, 2H), 2.92-3.50 (m, 6H partially overlapping with HDO signal), 1.11 (d, J=6.3 Hz, 3H). MS (ESI) m/z: Calculated; 429.2 Observed: 430.2 (M++1).

1. stirringthe mixture was stirred for 1 h at room temperature
2. customEvaporation and purification by flash chromatography (5% AcOH in CHCl3 and MeOH)
3. customsonicated
4. filtrationThe solids were collected by filtration
5. washwashed with water and Et2O