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. 2014 Sep 19;57(20):8664–8670. doi: 10.1021/jm5011397

Scheme 2. Synthesis of Aminoacylpyrrolidine 2.

Scheme 2

Reagents and conditions: (a) 9, TFA, DCM, 0 °C to rt, 24 h, 88%; (b) (i) 1-chloroethyl chloroformate, toluene, 110 °C, 3 h, (ii) MeOH, reflux, 30 min; (c) 12, EDCI, HOBt, DIPEA, DMF, 4 h, 55% over 2 steps; (d) LiBH4, THF, 3 h, 71%; (e) TFA, DCM, 2 h, 31%.