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. 2019 Aug 19;20(16):4050. doi: 10.3390/ijms20164050

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© 2019 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 2 — (i) VO(acac)₂, 70% t-BuOOH (2 equivalent), dry toluene, 25 °C, 12 h, 76%; (ii) RNH₂ (2 equivalent), LiClO₄ (1 equivalent), MeCN, 70–80 °C, 6 h, 40–88%; (iii) 5% Pd/C, H₂ (1 atm), MeOH, 25 °C, 24 h, 72%; (iv) 35% HCHO, Et₂O, 25 °C, 1 h, 60–70%; (v) 2% OsO₄/t-BuOH, 50% NMO/H₂O, acetone, 25 °C, 24 h, 61%; (vi) triphosgene (0.5 equivalent), dry pyridine (4 equivalent), dry CH₂Cl₂, 25 °C, 2 h, 60%; (vii) LiAlH₄ (2 equivalent), dry ether, 25 °C, 4 h, 80%, (viii) 3 M NaOH, DMSO, 80 °C, 2 h, 60%.