Sodium borohydride (47 mg) is added to 3-[(S)-1 -(4-bromo-phenyl)-ethyl]-1 -oxa-3- aza-spiro[5.5]undecane-2,9-dione (0.45 g) dissolved in tetrahydrofuran (4.5 mL) and water (0.6 mL) at room temperature. The mixture is stirred at room temperature for 2 h and then diluted with diethyl ether and acidified with 1 M aqueous hydrochloric acid. The organic phase is separated, washed with aqueous K2CO3 solution and brine, and dried (Na2SO4). The solvent is evaporated and the residue is submitted to HPLC on reversed phase (methanol/water) to give the title compound in a ca. 9:1 mixture with 3-[(S)-1 -(4-bromophenyl)ethyl]-frans-9-hydroxy-1 -oxa-3- azaspiro[5.5]undecan-2-one. Yield: 0.25 g (55% of theory); LC (method 1 ): tR= 3.42 min;
Mass spectrum (ESI+): m/z = 368/370 (Br) [M+H]+;
1H NMR (400 MHz, DMSO- d6) δ 1 .33-1 .55 (m, 4H) superimposed on 1 .47 (d, J = 7.1 Hz, 3H), 1 .55-1 .87 (m, 6H), 2.66-2.76 (m, 1 H), 3.13-3.22 (m, 1 H), 3.45 (mc, 1 H), 4.53 (d, J = 4.5 Hz, 1 H), 5.44 (q, J = 7.1 Hz, 1 H), 7.25 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H).
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