Hydrochloric Acid → HCID 58695815, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.471 g, 4.65 mmol) in anhydrous THF (10.0 mL) was added n-BuLi (2.91 mL, 4.65 mmol, 1.6 N in THF) at 0° C. The mixture was stirred at the temperature for 15 minutes and cooled to −78° C., followed by addition of a solution of 3-cyclohex-2-en-1-yl 8-ethyl 8-azabicyclo[3.2.1]octane-3,8-dicarboxylate (1-5) (1.30 g, 4.23 mmol) in THF (5.0 mL). After stirring at −78° C. for 30 min, TMSCl (0.459 g, 4.23 mmol) was added and the resulting solution was stirred at −78° C. for 1 h. The mixture was allowed to warm to room, temperature and stirred at 80° C. overnight. After cooling to room temperature, 2 N aqueous solution of HCl (10 mL) was added to the mixture. The mixture was stirred continued for 5 minutes, then partitioned between Et2O (50 mL) and 2 N HCl aqueous solution. The organic phase was washed with water, brine, dried over Na2SO4 and concentrated to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 10%-50% ethyl acetate/hexanes as eluent) afforded (1-6) as a white solid.

Provenance & Evidence