Potassium Carbonate → HCID 54420265, compound

Participants

Reaction Steps

A solution of 1-t-butoxycarbonyl-4-(prop-2-enyl)piperidine (330 mg, 1.46 mmol, from EXAMPLE 33, Step B) in 0.5 mL dry THF was cooled to 0° C. and a solution of 9-BBN (3.2 mL, 0.5 M in THF, 1.61 mmol) was added. The mixture was warmed to rt and stirred for 5 h. Potassium carbonate (405 mg, 2.93 mmol), 1,2-bis(diphenylphosphino) ferrocenyl palladium dichloride (60 mg, 0.073 mmol) and 3-bromobenzofurazan (292 mg, 1.46 mmol, from EXAMPLE 33, Step C) were added followed by 5 mL of dry DMF. The resulting mixture was heated to 55° C. overnight then diluted with 50 mL EtOAc. The solution was washed with H2O (3×) and sat'd NaCl then dried over Na2SO4 and concentrated. Flash chromatography (15 g silica, 5:1 v/v hexane/EtOAc eluant) afforded the 1-t-butoxycarbonyl derivative of the title compound. Heating in 1% conc. HCl/MeOH at 50° C. for 2h followed by removal of solvent and drying under vacuum afforded 155 mg (38%) of the title compound: 1H NMR (300 MHz, CD3OD) δ 1.31-1.42 (m, 4H), 1.6-1.75 (m, 1H), 1.842.0 (m, 4H), 2.9-3.1 (m, 4H), 3.3-3.4 (m, 2H), 7.25-7.3 (d, 1H), 7.47.5 (dd, 11), 7.7-7.75 (d, 1H).

Provenance & Evidence