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Two options for synthesis of amino nitrile 32 for the assembly of apalutamide. Reaction conditions: (a) MeNH2, THF; (b) PMBNH2, MeCN, microwave 190 °C; (c) TFA, CH2Cl2; (d) cyclobutanone, NaCN; (e) 18, CSCl2, MeCONMe2, 80 °C, then HCl, MeOH; (f) Me2NH–HCl, CDI, Et3N, CH2Cl2, rt; (g) Fe, AcOH, EtOAc, reflux; (h) cyclobutanone, TMSCN, AcOH, 80 °C.
