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. Author manuscript; available in PMC: 2014 Nov 1.
Published in final edited form as: Eur J Med Chem. 2013 Sep 22;69:10.1016/j.ejmech.2013.09.031. doi: 10.1016/j.ejmech.2013.09.031

Scheme 1. Synthesis of 6β-cinnamoyl morphinamines and codeinamines.

Scheme 1

(i) acetic anhydride, NaHCO3, H2O, r.t., 1 h. (ii) phthalimide, DIAD, Ph3P, benzene, r.t., 2h. (iii) hydrazine hydrate, EtOH. (iv) 1.1 eq. acyl chloride, Et3N, CH2Cl2, r.t., 2 h. (v) 1.1 eq. acyl chloride, Et3N, CH2Cl2, r.t., 2 h. then Na2CO3, H2O, MeOH, r.t., 12h.