Fig. 4 | Communications Chemistry

Fig. 4

From: Rivastigmine and metabolite analogues with putative Alzheimer’s disease-modifying properties in a Caenorhabditis elegans model

Fig. 4

Synthesis of rivastigmine analogues 9–11. a Synthesis of 9 and 11. Reagents and conditions: (i) CH3I, K2CO3, MeCN, rt; (ii) 32 wt% aq. HCl, MeOH, rt; (iii) ethyl(methyl)carbamic chloride, KOH, toluene, reflux; (iv) BBr3, CH2Cl2, −5 °C; (v) NH2OH·HCl, triethylamine, MeOH, reflux; (vi) 10 wt% Pd/C, H2, MeOH, rt; (vii) 10 wt% Pd/C, H2, HCHO (40 vol % aq. solution), MeOH, rt; (viii) 32 wt% aq. HCl, MeOH, rt. The synthesis of 2c and 5c is described in Fig. 1d. b Synthesis of 10. Reagents and conditions: (i) Ethyl(methyl)carbamic chloride, KOH, toluene, reflux; (ii) BBr3, CH2Cl2, −5 °C; (iii) TBDMS-Cl, DMAP, imidazole, CH2Cl2, 0 °C to rt; (iv) NH2OH·HCl, triethylamine, MeOH, reflux; (v) 10 wt% Pd/C, H2, MeOH, rt; (vi) 10 wt% Pd/C, H2, HCHO (40 vol % aq. solution), MeOH, rt; (vii) 32 wt% aq. HCl, MeOH, rt. The synthesis of acetophenone 10a is described in Supplementary Fig. 2

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