Modafinil enantiomers

Since the (S)-enantiomer of modafinil is a side product of the chiral separation of modafinil, it can potentially be recycled if a reduction method is employed. Two novel methods were developed by Fernandes and Romao.31 Using PhSiH3 and 5% Mo02C12 in refluxing THF or BH3-THF/ Mo02C12(5 mol%) at room temperature, treatment of sulfoxide 17 gave methyl ester of benzhydrylsulfanylacetic acid, 10 in 96% and 85% yield, respectively (Scheme 5). 

The Synthesis of Enantiomers of Modafinil and the Asymmetric Synthesis of Armodafinil... 

The active R-enantiomer of modafinil, also called armodafinil, is in development... 

Modafinil is a benzhydrylsulfinylacetamide wake-promoting agent for oral administration (1). It selectively targets neuronal pathways in the sleep/wake centers of the brain. It is well absorbed and its half-life is about 12-15 hours, which largely reflects the half-life of its levorotatory enantiomer. It... 

The chiral discrimination in the solid state of modafinil is particularly interesting because the API, the n-l and n-2 precursors (Figure 13.11) are respectively representative of the three binary systems represented in Figure 13.11. This case is also representative of the extensive problem of polymorphism and solvate formation for both the racemic compound and the pure enantiomer. ... 

O. Neckebrock, L. Courvoisier, S. Graf, G. Serrure, G. Coquerel, S. Rose, C. Besselievre, F. Mallet and A. J. V. Langevelde, Method for the production of crystalline forms crystalline forms of optical enantiomers of modafinil. US Pat., 2006135621, 22-06-2006, 2006. 

Modafinil contains a diphenylmethyl moiety and hence is traly dissimilar from the amfetamine structure. The (R)-enantiomer of modafinil appears to sustain higher... 

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