Iodoethane → HCID 68996667, compound

Participants

Reaction Steps

Ethyl iodide (50 μL, 0.63 mmol) was added to a solution of the amine from Step B (100 mg, 0.42 mmol) in methylene chloride (2 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 30 h. The mixture was quenched with a saturated solution of sodium bicarbonate and extracted with methylene chloride. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide) to afford tert-butyl 9-ethyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate (50 mg, 45%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.28 (br s, 1H), 3.99 (br s, 1H), 3.13-3.10 (m, 2H), 2.63 (q, J=7.0 Hz, 2H), 2.38-2.30 (m, 2H), 1.90-1.82 (m, 3H), 1.48-1.46 (m, 1H), 1.44 (s, 9H), 1.16-0.95 (m, 7H); MS (ESI+) m/z 269 (M+H).

Provenance & Evidence