1,4-diazabicyclo[3.2.2.]nonane and intermediates for the preparation thereof

• Main Authors: FRIEDMANN; ROBERT C, LACKEY; JOHN W, O'NEILL; BRIAN T
• Format: Patent
• Language: English
• Published: 25.06.1991
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

Processes and intermediates for preparing 1,4-diazabicyclo[3.2.2.]nonane including a process for the preparation of a compound of the formula III wherein R1 is C1-C4 alkyl or C1-C4 alkyl substituted with 1 to 6 halo groups; and R2 is hydrogen, naphthoyl, substituted naphthoyl, benzyl, substituted benzyl, benzoyl or substituted benzoyl, wherein each of said substituted naphthoyl, substituted benzyl, and substituted benzoyl is substituted with one to three substituents selected from the group consisting of halo, C1-C4 alkoxy and C1-C4 alkyl, comprising reacting a compound of the formula II wherein R1 and R3 are independently selected from C1-C4 alkyl and C1-C4 alkyl substituted with 1 to 6 halo groups with an alkyl stannane or a trialkyl aluminum and, if desired, reacting the resulting compound of the formula III wherein R2 is hydrogen with a reagent selected from the group consisting of the optionally substituted reagents naphthoyl chloride, naphthoyl bromide, naphthoyl triflate, benzoyl chloride, benzoyl bromide, benzoyl triflate, benzyl chloride, benzyl bromide and benzyl triflate, wherein the substituents on the substituted naphthoyl, substituted benzyl and substituted benzoyl are as defined above, to prepare the compound of the formula III, as defined above, wherein R2 is other than hydrogen.