Propanal → HCID 44610256, compound

Participants

Reaction Steps

A mixture of (R,Z)-5-(2-(3-aminopiperidin-1-yl)-3-chlorobenzylidene)thiazolidine-2,4-dione (122D) (100 mg, 0.27 mmol) and propionaldehyde (20.17 mg, 0.35 mmol) in CH2Cl2 (15 mL) was stirred at 50° C. for 20 min. before sodium triacetoxyborohydride (170 mg, 0.80 mmol) was added. The mixture was then stirred at 50° C. for 4 h. before sat'd aqueous K2CO3 (˜50 mL) was added to the mixture. This solution was poured into a separatory funnel and extracted with CHCl3/isopropanol (5/1) (2×50 mL). The combined organic extract was dried over anhydrous Na2SO4, filtered, and conc. in vacuo affording the product. It was purified with Gilson (0.1% TFA in water:0.1% TFA in CAN=30% to 80%; UV absorption at 322) to yield the title compound as a yellow solid (94 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (s, 1 H) 7.48 (d, 1 H) 7.41-7.34 (m, 1 H) 7.29 (t, 1 H) 3.67-3.58 (m, 2 H) 3.44-3.37 (m, 2 H) 3.03-2.78 (m, 5 H) 2.21 (brs, 1 H), 1.79 (d, 1 H) 1.61 (d, 6 H) 0.84-0.79 (m, 6 H). m/z 422.

Provenance & Evidence