Tert-Butylamine → HCID 58695796, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-cyclohexyl-8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid (1-7) (1.50 g, 4.85 mmol) in CHCl3 (60.0 mL) was slowly added oxalyl chloride (2.67 mL, 5.33 mmol, 2.0 N), followed by addition of DMF (3 drops) as a catalyst. After the bubbling ceased, the mixture was stirred for 30 min and the solvents were removed under vacuum. To the mixture was added t-BuNH2 (5.32 g, 72.7 mmol) and the resulting suspension was warmed up to 80° C. overnight. The solvents were removed under vacuum; the reaction was quenched with 1 N HCl, and then extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent) afforded (1-8) as a white solid.

Provenance & Evidence