Isobutylamine → HCID 28165295, compound

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Reaction Steps

N-t-butoxycarbonylvaline (2.2 g, 10 mmol) is dissolved in, dry THF under nitrogen, and to this is added 2.0 g (12 mmol) of carbonyldiimidazole. After this mixture is stirred for 50 min, 2.0 mL (20 mmol) of isobutylamine is added. After 1 week, the mixture is concentrated, dissolved in ethyl acetate, and washed successively with aqueous potassium hydrogen sulfate, water, and brine. It is dried over anhydrous sodium sulfate and concentrated to 2.27 g (8.3 mmol, 83%) of the title compound as a white solid. NMR (CDCl3) δ 6.0 (br, 1H), 5.07 (br d, 1H), 3.83 (m, 1H), 3.10 (m, 2H), 2.14 (m, 1H), 1.77 (m, 1H), 1.44 (s, 9H), 1.01-0.90 (overlapping d, 12H). HRMS (ESI) calcd for C14H28N2O3+H1 273.2178, found 273.2180

Provenance & Evidence