Triethylamine → HCID 17819432, compound

Participants

Reaction Steps

A Parr bottle was charged with palladium (II) hydroxide (800 mg), a solution of N-butoxycarbonyl-1-iodo-2-amino-3-fluoro-3-methyl-n-butane (3.26 g, 9.8 mmol) in ethanol (80 mL) and triethylamine (0.99 g, 9.8 mmol). The reaction mixture was placed under hydrogen gas (50 psig) and shaken for 20 hours. The mixture was filtered through Celite® and evaporated. The residue was dissolved in diethyl ether (100 mL) and washed with 1N aqueous HCl (2×50 mL), water (2×50 mL), and then dried (MgSO4). Filtration and evaporation gave a residue that was chromatographed (silica gel, diethyl ether/hexane (3/1)) to afford 1.80 g of N-butoxycarbonyl-2-amino-3-fluoro-3-methyl-n-butane: 1H NMR (CDCl3) δ4.65 (br, 1H), 3.70 (br m, 1H), 1.45 (s, 9H), 1.39 (d, 3H), 1.32 (d, 3H), 1.18 (d, 3H) ppm.

Provenance & Evidence