2-Bromonaphthalene → 3-Hydroxy-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic Acid Tert-Butyl Ester

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 6.20 g (29.9 mmol) 2-bromonaphthalene and 125 mL THF is added 12 mL of 2.5 M n-BuLi/hexanes. After stirring at −78° C. for 30 mins a solution of 6.40 g (28.4 mmol) 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester and 14 mL THF is added dropwise. The reaction is allowed to proceed at −78° C. for 30 mins and then warmed to 23° C. over 6 h. After quenching with 100 mL 1N NaOH and extraction with 3×100 mL of EtOAc, the combined organics are washed with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered, and the volatiles removed. Flash chromatography in SiO2 gel, eluting with hexanes/EtOAc (4/1 to 1/1) gives 7.00 g (19.8 mmol, a 66% yield) of the title compound as a white solid. MS (ES) m/z 354 (M++H, 100).

Provenance & Evidence