Carbonate Ion → Pioglitazone, (R)-

Participants

Reaction Steps

MP-Carbonate (389 mg, 1.06 mmol) was added to a solution of (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione trifluoroacetate (100 mg, 0.21 mmol) in MeOH (100 mL) and stirred at RT for 2 h, filtered and the resin washed with MeOH (3×10 mL). The filtrate was concentrated in vacuo to afford the title compound (35 mg, 47%). e.e. (Method 2) 92.90%, Rt 6.27 min. 1H NMR (400 MHz, DMSO-d6): δ 12.44-11.11 (1 H, bs), 8.34-8.29 (1 H, d, J 1.9), 7.55-7.49 (1 H, dd, J 2.2, 7.9), 7.24-7.20 (1 H, d, J 7.8), 7.12-7.05 (2 H, d, J 8.6), 6.84-6.77 (2 H, d, J 8.6), 4.78-4.71 (1 H, dd, J 4.3, 9.1), 4.30-4.19 (1 H, d, J 4.3), 3.24-3.18 (2 H, d), 3.11-3.03 (2 H, t, J 6.6), 3.00-2.92 (1 H, dd, J 9.2, 14.2), 2.59-2.50 (2 H, q, J 7.6), 1.17-1.09 (3 H, t, J 7.7).

Provenance & Evidence