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. Author manuscript; available in PMC: 2016 Sep 1.
Published in final edited form as: Bioorg Med Chem. 2015 Jul 16;23(17):5709–5724. doi: 10.1016/j.bmc.2015.07.013

Scheme 1.

Scheme 1

Synthesis of 7-alkoxytetrahydroisoquinoline derivatives

Reagents and Conditions: (a) (i) 3,4-Dimethoxyphenylacetic acid, BOP, iPr2EtN, DMF; (ii) R-I or R-Br, K2CO3, DMF; (b) (i) POCl3, toluene; (ii) NaBH4, MeOH; (c) (i) MeOCOCl, iPr2EtN, CH2Cl2; (ii) R-I or R-Br, K2CO3, DMF; (d) 3,4-dimethoxyphenylacetaldehyde, TFA; (e) KOH, NH2NH2.H2O, (CH2OH)2; (f) BrCH2CONHBn, iPr2EtN, Bu4NI, DMF.