HCID 22716444, compound → HCID 22716425, compound

Participants

Reaction Steps

Compound 39 (50 mg, 0.112 mmol) was hydrogenated in ethyl acetate (40 mL) at 30 lb./sq. in. using 10% palladium on carbon (15 mg) as catalyst for 16 hours. The solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration of the ethyl acetate solution in vacuo gave a crude product. Column chromatography was performed using a 35:65 mixture of hexanes:ethyl acetate as eluting solvent to give two compounds. The compound having the higher Rf material on thin layer chromatography was isolated as compound 41 (34 mg, 73%); IR (KBr) 3446, 2932, 1610, 1509, 1461, 1421, 1254 cm−1; 1H NMR (CDCl3) δ3.90 (3H, s), 4.01 (3H, s), 4.02 (3H, s), 5.08 (2H. s), 6.42 (1H, s), 6.87 (1H, s), 7.12 (1H, s), 7.15 (1H, s), 7.33-7.48 (6H, m), 7.71-7.75 (2H, m); 13C NMR δ56.40, 56.42, 56.48, 73.07, 101.48, 106.59, 106.78, 119.09, 119.96, 126.24, 126.78, 127.29, 128.16, 128.20, 128.45, 128.90, 129.86, 135.56, 138.19, 138.88, 141.70, 150.07, 150.30, 150.92; HRMS (EI) calcd for C26H25NO4 m/z: 415.1784; found: 415.1775.

Provenance & Evidence