HCID 11096167, compound → HCID 11830202, compound

Participants

Reaction Steps

To a solution compound (35) from Example 21 (1.00 mmol) in anhydrous diethyl ether (5 ml) at 0° C. was added slowly, dropwise, 3.0 M methylmagnesium bromide (1.10 mmol). The resulting solution was stirred for 10 minutes and the reaction was then quenched by addition of pH7 buffer. Diethyl ether (20 ml) was added, whereafter the solution was washed with water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered. The solvent was removed under reduced pressure to afford the title compound (41) as a clear oil which was subjected to flash chromatography on silica gel. [α]D21 -68.9 (c 1.61, CHCl3); νmax (CHCl3)/cm-1 1742 s (C=O), δH (300 MHz; CDCl3) 7.34-7.23(5H, m, Ph), 4.92 (1H, q, J=7.2, PhCHCH3), 3.51 (1H, m, CH3CHCH2); 2.97, 2.46 (2H, ABX system, JAB =14.4, JAX =5.1, JBX =2.4, CH2CO), 1.63 (3H, d, J=7.2, PhCHCH3), 1.25 (3H, d, J=6.1, CH3CHCH2); δC (50 MHz; CDCl3) 166.90 (C=O), 140.67 (Ph:Cipso), 128.85, 127,18 (Ph:Cortho,Cmeta), 127.77 (Ph: Cpara), 51.78, 47.18 (CHN), 43.45(CH2CO), 20.65, 19.25 (NCHCH3); m/z (CI) 190 (MH+, 100%), 174(5), 132 (10), 105 (8); (Found: C, 76.02; H, 7.98; 7.07. C12H15NO requires C, 76.16; H, 7.99; N, 7.40%).

Provenance & Evidence