Hydrochloric Acid → HCID 11096167, compound

Participants

Reaction Steps

A solution of compound (29) from Example 14 (1.00 mmol) was stirred in a saturated solution of gaseous hydrogen chloride in methanol for 30 minutes. The solvent was then removed under reduced pressure. This procedure was repeated until no starting material remained. The white solid residue was diluted with ethyl acetate (30 ml), washed with saturated aqueous sodium bicarbonate (2×30 ml), water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered, and the solvent was evaporated under reduced pressure to give the title compound (35) as a clear oil. [α]D21 -45.5 (c 1.95, CHCl3); νmax (CHCl3)/cm-1 1736 s (C=O); δH (300 MHz; CDCl3) 7.34-7.20 (5H, m, Ph), 3.88 (1H, q, J=6.5, PhCHCH3), 3.67 (3H, s, OCH3), 2.99 (1H, m, CH3CHCH2), 2.47, 2.38 (2H, ABX system, JAB =14.8, JAX =5.4, JBX =6.5, CH2CO), 1.33 (3H, d, J=6.5 PhCHCH3), 1.06 (3H, d, J=6.4, CH3CHCH2); δC (50 MHz; CDCl3) 173.01 (C=O), 146.29 (Ph:Cipso), 128.63, 126.70 (Ph:Cortho, Cmeta), 127.07 (Ph:Cpara), 55.15, 47.69 (CHN), 51.30 (OCH3), 40.52 (CH2CO), 24.54, 21.34 (NCHCH3); m/z (CI) 222 (MH+, 100%), 206 (15), 148 (10), 118 (5), 105 (10); (Found: C, 70.48; H, 8.80. C13H19NO2 requires C, 70.56; H, 8.65%).

Provenance & Evidence