635298-66-7Relevant articles and documents
Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: Formal syntheses of natural epibatidine and its enantiomer
Moreno-Vargas, Antonio J.,Vogel, Pierre
, p. 3173 - 3176 (2007/10/03)
The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2- one (±)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine.