Water → 6-Benzyl-4-oxo-4,4a,5,6,7,7a,8,9-octahydro-1,6-diaza-cyclopenta[f]azulene-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

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반응 단계

4-Oxo-7,8-dihydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (2.92 g, 9.15 mmol), LiF (296 mg, 11.4 mmol) and benzyl-methoxymethyl-trimethylsilanylmethyl-amine are mixed together in CH3CN (10 ml). The reaction mixture is sonicated under N2. The water bath is kept under 35° C. with ice. After 6 h, solvents are removed in vacuo. The residue is put on a column (1:1 EtOAc hexanes) to afford the title compound as clear oil, which solidified upon standing. 1H NMR (400 MHz, CDCl3) δ 1.23 (3H, t), 1.56 (9H, s), 1.88-2.00 (2H, m), 2.65 (1H, m), 2.92-3.02 (4H, m), 3.24 (1H, m), 3.50-3.59 (3H, m), 4.06 (1H, q), 4.19 (2H, q), 7.18-7.27 (5H, m), 7.62 (1H, s). MS (ES+) 453 (M+1) Step 2: 6-Benzyl4-oxo-4,4a,5,6,7,7a,8,9-octahydro-1H-1,6-diaza-cyclopenta[f]azulene-3-carboxylic acid pyridin-2-ylamide

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