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. Author manuscript; available in PMC: 2021 Mar 4.
Published in final edited form as: ACS Chem Neurosci. 2020 Feb 17;11(5):674–701. doi: 10.1021/acschemneuro.0c00003

Scheme 14. Synthesis of 9b-e from aldehyde 50.a.

Scheme 14.

aReagents and conditions: (a) MeNH2·HCl, NaBH3CN, MeOH, rt, overnight, (48%); (b) BnNH2·HCl, NaBH3CN, MeOH, (70%); (c) NaBH4, MeOH, rt, 30min, (83%); (d) NaO2Cl, THF:H2O:tert-BuOH 1:1:1, 2-methyl-butene, phosphate buffer, (94%); (e) TFA, DCM, rt, overnight, (53–99%).