Scheme 1From: Design, synthesis, and preliminary evaluation of a potential synthetic opioid rescue agentSynthetic route to C14 analogues 14, 16, and 20–22. Reagents and conditions (a) K2CO3, BnBr, DMF; (b) (CH2OH)2, p-TSA, toluene; (c) NaH, dipropyl sulfate (32a) or (3-bromoprop-1-en-1-yl)cyclohexane (32b), DMF; (d) conc. HCl, MeOH; (e) NaH, allyl bromide, DMF; (f) Pd/C, H2, THF; (g) TBDMSCl, imidazole, DMF; (h) Propionic anhydride, Et3N, toluene; (i) KF, MeOH, DCMBack to article page