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. Author manuscript; available in PMC: 2015 May 19.
Published in final edited form as: Bioorg Med Chem Lett. 2009 Mar 28;19(10):2722–2727. doi: 10.1016/j.bmcl.2009.03.118

Scheme 2.

Scheme 2

Reagents and conditions: (a) paraformaldehyde, p-TsOH·H2O, toluene, reflux, 2 h, 98%; (b) HNR1R2, HOBt, EDC·HCl, DMF, 0 °C–rt, overnight, 80–98%; (c) CsF, CF3Si(CH3)3, THF, sonication, rt, 3 h then MeOH, rt, 30 min then NaBH4, rt, overnight, 48–61%; (d) H2, Pd/C (10%), MeOH, rt, overnight, 100%; (e) Cbz-AA-OH, HOBt, EDC·HCl, DMF, 0 °C–rt, overnight; (f) Dess–Martin periodinane, CH2Cl2, rt, 16 h, EtOAc then filtration through Celite followed by HPLC purification.