Crystal structures of three cyclohexane-based γ-spirolactams: determination of configurations and conformations

• Main Authors: Tobias Krueger, Alexandra Kelling, Torsten Linker, Uwe Schilde
• Format: Article
• Language: English
• Published: BMC 2019-05-01
• Series: BMC Chemistry
• Subjects: 2-Azaspiro[4.5]deca-1-ones; Cis- and trans-form; Configuration; Conformation; Lactams
• Online Access: http://link.springer.com/article/10.1186/s13065-019-0586-7

Abstract The title compounds, 2-azaspiro[4.5]deca-1-one, C9H15NO, (1a), cis-8-methyl-2-azaspiro[4.5]deca-1-one, C10H17NO, (1b), and trans-8-methyl-2-azaspiro[4.5]deca-1-one, C10H17NO, (1c), were synthesized from benzoic acids 2 in only 3 steps in high yields. Crystallization from n-hexane afforded single crystals, suitable for X-ray diffraction. Thus, the configurations, conformations, and interesting crystal packing effects have been determined unequivocally. The bicyclic skeleton consists of a lactam ring, attached by a spiro junction to a cyclohexane ring. The lactam ring adopts an envelope conformation and the cyclohexane ring has a chair conformation. The main difference between compound 1b and compound 1c is the position of the carbonyl group on the 2-pyrrolidine ring with respect to the methyl group on the 8-position of the cyclohexane ring, which is cis (1b) or trans (1c). A remarkable feature of all three compounds is the existence of a mirror plane within the molecule. Given that all compounds crystallize in centrosymmetric space groups, the packing always contains interesting enantiomer-like pairs. Finally, the structures are stabilized by intermolecular N–H···O hydrogen bonds.