m-Chloroperbenzoic acid → 6-(Tert-butoxycarbonyl)-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine 1-oxide

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Reaction Steps

3-Chlorobenzoperoxoic acid (241 mg, 1.4 mmol) was added to a solution at 0° C. of tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (250 mg, 0.93 mmol, see Example 1 procedure) in CHCl3 (3 mL). The reaction mixture thus obtained was warmed to room temperature and stirred overnight. After concentration, the residue was purified by flash chromatography on silica gel eluting with 0% to 80% EtOAc in hexane to give the title compound (150 mg, 56.6% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.51 (9H, s), 3.11 (2H, m), 3.77 (2H, t, J=6.16 Hz), 4.60 (2H, s), 6.99 (1H, d, J=8.41 Hz), 7.40 (1H, d, J=8.41 Hz) ppm; LC/MS m/z: 285 (M+1).

Provenance & Evidence