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Synthesis of the amino nitrile 26 (top) and amino ester 29 (bottom) for the assembly of enzalutamide. Reaction conditions: (a) CrO3, H5IO6, CH3CN, CH2Cl2; (b) SOCl2, DMF, then MeNH2; (c) Fe, AcOH, EtOAc, reflux; (d) 2-cyano-2-hydroxypropane, MgSO4, EtOAc, 80 °C; (e) 13, DFM, microwave 100 °C; (f) SOCl2, DMF (cat), 2-PrOAc, 60 °C, then MeNH2; (g) 2-aminoisobutyric acid, CuI, K2CO3, 2-acetylcyclohexanone, DMF, H2O, 105 °C; (h) MeI, K2CO3, DMF, H2O, 40 °C; 13, DMSO, 2-PrOAc, 83–83 °C.
