HCID 59662197, compound → HCID 59662171, compound

Participants

Reaction Steps

Compound 4-3 (2.73 g, 7.76 mmol), EtOH/AcOH (1:1, 60 mL) and PtO2 (0.895 g) were shaken in a Parr apparatus (15 psig of hydrogen) for 10 hrs. The reaction mixture was filtered thru Celite®, washing with ethanol. The solution was concentrated, and the residue was diluted with dichloromethane and washed with saturated NaHCO3. The aqueous layer was again extracted with dichloromethane, and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The product was purified by flash chromatography (gradient elution with 15-50% ethylacetate (0.1% TEA) in heptane. The desired product Compound 4-4 was isolated as thick colorless oil (2.55 g, 93%). 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=2.3 Hz, 1H), 7.43 (d of d, J=8.5 and 2.3 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 4.22 (m, 2H), 3.91 (s, 3H), 3.52 (m, 1H), 2.82 (m, 2H), 2.8-1.5 (m, 4H), 1.48 (s, 9H); MS (ES+) m/z 253.8 (M-Boc+1); HRMS (FAB+) Calcd for C18H23ClNO4: 352.1316. Found: 352.1329.

Provenance & Evidence