Allylamine → (S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate

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Reaction Steps

A 500 mL round bottom flask was charged with (S)-2-(tert-butoxycarbonylamino)butanoic acid (5.0 g, 0.025 mol), 1-hydroxybenzotriazole hydrate (3.4 g, 0.025 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (7.2 g, 0.038 mol), and dichloromethane (125 mL). Triethylamine (7.6 mL, 0.055 mol) and allylamine (1.9 g, 0.025 mol) were added and the resulting mixture stirred at room temperature for 22 h. The resulting mixture was then diluted with dichlormethane (300 mL), washed 1× with 1N HCl (200 mL), 1× with 1N NaOH (200 mL), and 1× with water (200 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo to yield (S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.15-5.23 (m, 2H), 4.03-4.19 (m, 1H), 3.88-3.92 (m, 2H), 1.82-1.94 (m, 1H), 1.60-1.72 (m, 1H), 1.45 (s, 9H), and 0.96 (t, J=7.4 Hz, 3H).

Provenance & Evidence