HCID 53765206, compound → HCID 19002305, compound

Participants

Reaction Steps

A total of 3.4 g (9.2 mmol) of 38 in 100 mL MeOH was hydrogenated at 40 psi H2 over 300 mg 10% Pd.C. Hydrogen was replenished at t=15, 60, 135, 210 and 255 minutes and 300 mg additional 10% Pd, C was added at t=135 and 255 minutes and the reaction terminated at t=6 hours. The mixture was filtered through celite and rotovapped (30° C.) to yield 39 as a clear colorless oil (2.97 g, 95%). The oil crystallized from ether yielding white crystals, mp 94°-100° C. (soften 77° C.). 1H NMR (250 MHz, DMSO-d6) δ: 7.34 (d, 2H, J=7.5 Hz, aromatic), 7.15 (d, 2H, J=7.5 Hz, aromatic), 6.16 (br s, 1H, OH) , 4.89 (d,1H, J=13.0 Hz, PCH), 3.93 (m, 4H, OCH2), 3.59 (m, 1H, Hα), 3.57 (s, 3H, CO2CH3), 2.87 (dd, 1H, J=13.4, 6.7 Hz, Hβ), 2.76 (dd, 1H, J=13.4, 7.2 Hz, Hβ) , 1.17 (t, 3H, J=7.0 Hz, CH3), 1.13 (t, 3H, J=7.0 Hz, CH3), mp 94°-100° C.; FABMS m/z 346.1 (M+H)+.

Provenance & Evidence