Toluene → Tert-butyl-6-cyano-6-(pyridine-2-YL)-3-azabicyclo[3.1.0]hexane-3-carboxylate

Participants

Reaction Steps

To a solution of 3 (700 mg, 3.36 mmol) in toluene (16 mL) at 0° C. was added 2-fluoropyridine (326 mg, 3.36 mmol) and a solution of KHMDS (0.5M in toluene, 6.72 mL, 3.36 mmol). The reaction was warmed to room temperature and stirred for 18 h. The crude reaction was purified by column chromatography using 0 to 60% EtOAc in hexanes to afford 10 (390 mg, 41%) as a clear oil; 1H-nmr (400 MHz, CDCl3) δ 8.46 (d, J=4.0 Hz, 1H), 7.75-7.66 (m, 2H), 7.17 (td, J=7.0, 1.5 Hz, 1H), 3.95 (d, J=12.5 Hz, 1H), 3.86 (d, J=12.5 Hz, 1H), 3.81-3.71 (m, 2H), 2.69 (s, 2H), 1.88 (d, J=5.0 Hz, 4H), 1.48 (s, 9H); LC-MS (214 nM) 2.96 min (>98%), m/z 286.1 [M+H].

Provenance & Evidence