Synthesis of 3-Amino-2,2-dimethyl-8-thia-1-azaspiro[4.5]decane

Abstract

The synthesis of 3-amino-2,2-dimethyl-8-thia-1-azaspiro[4.5]decane is described. Key steps include the addition of prenyl magnesium bromide to a 4-methoxybenzylimine without reversal of stereochemistry and the iodine-initiated aminocyclization to form the azaspirocycle.

Keywords:

• Grignard reactions
• heterocycle
• iodoaminocyclization
• prenylation
• spiro compound

ACKNOWLEDGMENTS

Financial support from the National Institutes of Health (R01 DA017201) and the Michigan Technological University Chemistry Department; the assistance from Mr. Jerry L. Lutz (NMR), Mr. Shane Crist (computation), and Mr. Dean W. Seppala (electronics); and an NSF equipment grant (CHE-9512445) are all gratefully acknowledged.