Lithium Hydroxide → Benzyl(cis)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate

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Reaction Steps

To a solution of benzyl(cis)-3-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-4-[(4-nitrobenzoyl)oxy]pyrrolidine-1-carboxylate (3.17 g) in tetrahydofuran (38 ml) and methanol (3 ml) was added LiOH (1M(aq), 38 ml). The reaction mixture stirred 45 min and was poured into saturated sodium bicarbonate (100 ml). The aqueous layer was extracted ethyl acetate (2×200 ml), dried MgSO4, filtered and concentrated. MPLC chromatography on a biotage 40M column with 20–60% ethyl acetate/heptane provided the title compound as an oil (1.225 g, 50%): 1H NMR (400 MHz, CDCl3) δ) 7.50, 7.46–7.25, 5.18, 4.99, 4.89, 4.70, 4.51, 4.04, 3.75–3.59, 3.42–3.35, 2.70, 2.47, 2.19, 1.14; HRMS (FAB) calcd for C26H28Cl2N4O3+H 515.1616, found 515.1641. Anal. Calcd for C26H28Cl2N4O3: C, 60.59; H, 5.48; N, 10.87. Found: C, 60.32; H, 5.79; N, 10.54.

Provenance & Evidence