HCID 90388059, compound → HCID 90388303, compound

Participants

Reaction Steps

To compound 36 (120 mg, 0.44 mmol) in pyridine (40 mL) was added Pd/C (100 mg) at room temperature. Hydrogenation was carried out under 60 psi H2. After 3 h, the pressure was released and the mixture was filtered through Celite® 545 which was washed with EtOAc (100 mL). Solvents were removed and the residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to give compound 53 (120 mg, 4aR:4aS ratio 2.5:1): 1H NMR (CDCl3) 4aR diastereoisomer δ 3.66 (t, J=8.5 Hz, 1H), 2.58 (t, J=14.0 Hz, 1H), 2.24-0.79 (m, 23H), 0.72 (s, 3H); 13C NMR (CDCl3) δ 213.2, 81.8, 45.3, 44.8, 43.3, 43.0, 40.2, 38.8, 38.6, 36.7, 31.1, 30.4, 29.1, 29.0, 27.4, 25.7, 11.4.

Provenance & Evidence