Triethylamine → Tert-butyl 3-(methanesulfonyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester (7.55 g, 33.2 mmol), triethylamine (5.1 mL, 37 mmol), and 4-dimethylaminopyridine (36 mg, 0.3 mmol) was dissolved in 100 mL of dichloromethane and cooled to 5° C. in an ice bath. Methanesulfonyl chloride (2.6 mL, 33.2 mmol) was added to the solution dropwise and the reaction warmed to room temperature and stirred at room temperature for 18 hours. The reaction washed with water and brine, dried over anhydrous sodium sulfate, and the solvent removed to afford 3-methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester as a clear yellow oil (10.2 g); 1H NMR (300 MHz, DMSO-d6): 5.09-5.01 (m, 1H), 4.28 (s, 1H), 4.22 (s, 1H), 3.01 (s, 3H), 2.20-1.97 (m, 6H), 1.71-1.66 (m, 2H), 1.46 (s, 9H).

Provenance & Evidence