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2-Phenylpyrrolidine (PPD) is a nicotine analogue that keeps nicotine's two-ring motif but replaces the pyridine with a phenyl group, making it closely related to nornicotine^[1].

The Journal of Organic Chemistry, 45, p. 1515, 1980 DOI: 10.1021/jo01296a036
Synthetic Communications, 25, p. 3789, 1995 DOI: 10.1080/00397919508011452
Tetrahedron Letters, 25, p. 527, 1984 DOI: 10.1016/S0040-4039(00)99928-3

The 2-phenylpyrrolidine series was built from a pyrroline formed by reacting lithiated N-pyrrolidinone with Boc-2-fluoro-4-bromoaniline, which was then subjected to sodium borohydride reduction, Eschweiler–Clarke N-methylation and acidic deprotection to give an intermediate that was elaborated into the pyrrolidinone framework with N-Boc-homoserine lactone and trimethylaluminium^[2].

[1] Martin, D. E., Robertson, E. G., MacLellan, J. G., Godfrey, P. D., Thompson, C. D., & Morrison, R. J. S. (2009). A Spectroscopic Study of Nicotine Analogue 2-Phenylpyrrolidine (PPD) Using Resonant Two-Photon Ionization (R2PI), Microwave, and 2D NMR Techniques. Journal of the American Chemical Society, 131(7), 2638–2646. https://doi.org/10.1021/ja807995n
[2] Young, R. J., Adams, C., Blows, M., Brown, D., Burns-Kurtis, C. L., Chan, C., Chaudry, L., Convery, M. A., Davies, D. E., Exall, A. M., Foster, G., Harling, J. D., Hortense, E., Irvine, S., Irving, W. R., Jackson, S., Kleanthous, S., Pateman, A. J., Patikis, A. N., … Watson, N. S. (2011). Structure and property based design of factor Xa inhibitors: Pyrrolidin-2-ones with aminoindane and phenylpyrrolidine P4 motifs. Bioorganic & Medicinal Chemistry Letters, 21(6), 1582–1587. https://doi.org/10.1016/j.bmcl.2011.01.131