HCID 89498794, compound → HCID 86680951, compound

Participants

Reaction Steps

To a solution of compound 4 (0.22 g, 0.468 mmol) in methanol 20 mL and 1 N HCl (5 mL) was added palladium (10%) on carbon (0.08 g, 0.752 mmol) (Degussa wet catalyst). The flask was attached to a Parr 3911 hydrogenation apparatus, evacuated via a water aspirator, and filled with H2 (40 psi). After shaking for 18 hours at room temperature, the mixture was filtered through celite with MeOH eluent. The celite pad then was washed with methanol (2×) and 2 M NH3 in dioxane (2×). The filtrate was concentrated, diluted with water, and washed with EtOAc (1×). The aq layer was made basic with satd. aq. NaHCO3 and extracted with CH2Cl2(2×) and EtOAc (3×). The combined layers were dried over MgSO4, concentrated to an oil, and used without further purification. HPLC purity 89% (tR=4.88 min). NMR (500 MHz, CDCl3) δ 6.9 (s, 1H), 6.7-6.8 (m, 2H), 4.6 (d, 1H), 4.3 (s, 4H), 2.8-2.9 (m, 1H), 2.4-2.5 (m, 6H), 2.4 (m, 3H), 1.7-1.8 (m, 5H). ESI-MS m/z 293.1 (M+H+).

Provenance & Evidence