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. 2019 Nov 14;6(6):064701. doi: 10.1063/1.5122849

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© 2019 Author(s).

2329-7778/2019/6(6)/064701/20

All article content, except where otherwise noted, is licensed under a Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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SCHEME 4. — Synthesis of 4(5)-(hydroxymethyl)imidazole derivatives. Reaction conditions for the scheme: (a) NaN₃, DMSO, 50 °C; (b) 1. Pd/C, H₂, MeOH and 2. Cbz-Cl, Et₃N, DCM; (c) HCl_(g), EtOH, 2 h; (d) 1. AcCl/EtOH and 2. NH₃/MeOH; (e) dihydroxyacetone, NH₄OH/i-PrOH, microwave, 90 °C, 1 h; (f) dihydroxyacetone, NH₃.H₂O; (g) Pd/C, H₂, MeOH; (h) Ac₂O, DCM, MeOH, rt; (i) ClCOR₂, DCM, MeOH, Et₃N; (j) R₂COH, NaCNBH₃, MeOH, AcOH; (k) ClCOR₂, NaOH, H₂O/DCM; (l) ClCO₂CH₃, DCM, TEA; (m) TBDPS-Cl, Et₃N, DCM; (n) TBAF, THF; (o) TFA, DCM; and (p) HCl/dioxane.