HCID 11747380, compound → HCID 15336556, compound

Participants

Reaction Steps

A solution of 4a (1.04 g, 4 mmol) in 100 mL of EtOH was hydrogenated at 60 psi hydrogen pressure (Parr shaker) over 200 mg of 5% Pd/C for 5 h. Filtration, concentration, and flash chromatography of the residue (30% ethyl acetate in hexanes) gave 1.03 g (98%) of 4d: IR (neat) 2955, 1599, 1477, 1084, 1031 cm-1 ; 1H NMR δ7.20 (d, 1H, J=8.3 Hz), 6.50 (d, 1H, J=8.3 Hz), 4.01 (m, 4H), 3.89 (s, 3H), 2.98 (m, 2H), 2.78 (dd, 1H, J=16.0, 2.4 Hz), 2.01 (m, 2H), 1.67 (m, 2H), 1.40 (m, 2H), 0.96 (t, 3H, J=7.2 Hz); 13C NMR δ162.0, 155.7, 139.6, 121.3, 107.9, 107.7, 64.4, 53.0, 39.5, 38.0, 37.2, 35.9, 19.9, 14.3; MS m/z 263 (M+).

Provenance & Evidence