HCID 71499446, compound → HCID 71499427, compound

Participants

Reaction Steps

A 1 dram vial equipped with a stir bar is charged with 14.9 mg (0.037 mmol, 1 equiv.) of starting material 50 followed by 370 μL of methanol. The vial was flushed with argon, and 8.5 mg of palladium (5 wt % on activated carbon, 0.004 mmol, 0.10 equiv.) was added. The vial was then flushed with hydrogen, and a balloon contained hydrogen was affixed to the vial through a rubber septum cap. The mixture was stirred for 25 min at which time the mixture was filtered through Celite®. The filter cake was rinsed with copious amounts of methanol, and the collected filtrate was concentrated. The crude product was purified by silica gel chromatography (Rf=0.25 in 9:1 hexane:ethyl acetate), affording 14.5 mg (92% yield) of 55 as a clear oil. 1H NMR (500 MHz, CDCl3) δ ppm 5.69 (s, 1H), 4.58 (dd, J=6.9, 52.4 Hz, 2H), 3.80 (s, 3H), 3.59 (dd, J=5.4, 11.3 Hz, 1H), 3.33 (s, 3H), 3.15 (s, 1H), 2.20 (dd, J=5.4, 13.4 Hz, 1H), 1.79 (dt, J=4.5, 12.6 Hz, 1H), 1.72 (dd, J=11.3, 13.3 Hz, 1H), 1.66-1.48 (m, 3H), 1.31-1.14 (m, 4H), 1.14-1.05 (m, 1H), 0.90-0.85 (m, 15H). HRMS-ESI (m/z): [M+K]+ calculated for C24H40O5, 447.2507. found 447.2511.

Provenance & Evidence