(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide → (3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

Participants

Reaction Steps

A solution of 22 (6.5 g, 15 mmol) in 6N-HCl aq (100 ml) was heated at reflux for 10 hours. The resulting solution of sodium hydroxide (NaOH) (24 g) in water (100 ml) and extracted with CH2Cl2 (100 ml) four times. The combined extracts were dried over Na2SO4 and concentrated. The clude was purified by recrystallization from EtOH to give 23 (1:1 mixture at 6-position; 10 mmol, 68%).

Provenance & Evidence