Hydrochloric Acid → (8bS)-N-[(1R)-2,3-dihydro-1H-inden-1-yl]-7-[2-(4-fluorophenyl)ethyl]-6,13-dioxo-5,8b,9,10,11,13-hexahydro-6H-benzo[c]pyrrolizino[2,1-f][2,7]naphthyridine-3-carboxamide

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Reaction Steps

A solution of ethyl (9aS)-4-(4-{[(1R)-2,3-dihydro-1H-inden-1-ylamino]carbonyl}-2-nitrophenyl)-2-[2-(4-fluorophenyl)ethyl]-5-oxo-7,8,9,9a-tetrahydro-5H-pyrido[2,3-a]pyrrolizine-3-carboxylate Example 53 (0.068 g, 0.11 mmol, 1 equiv) in a 1:1 mixture of ethanol and H2O (4.0 mL) was treated with sodium dithionite (0.057 g, 0.33 mmol, 3 equiv). After 12 h, the reaction was acidified with 1 N HCl to ca. pH 5. Extraction with EtOAc (3×3 mL) was followed by drying (Na2SO4), and concentration. Trituration with acetone gave 0.048 g (80%) of analytically pure title compound as a light brown solid: 1H NMR (DMSO-d6, 400 MHz) δ 10.80 (s, 1H); low resolution MS (ES+) m/e 573 (MH+); RP-HPLC (Dynamax C-18 25 cm×4.1 mm; 50–100% CH3CN in H2O with 0.1% TFA buffer; 30 minutes; 1 mL/min) tr=11.39 min, 97% purity.

Provenance & Evidence