Huperzine B synthesis
- Product Name:Huperzine B
- CAS Number:103548-82-9
- Molecular formula:C16H20N2O
- Molecular Weight:256.34
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Yield:-
Steps:
Multi-step reaction with 12 steps
1.1: lithium diisopropyl amide
2.1: tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; potassium carbonate
3.1: lithium diisopropyl amide / -25 °C
4.1: sodium tetrahydroborate
5.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C
6.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate
7.1: tetrahydrofuran / 3 h / -25 °C / Inert atmosphere
8.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
9.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / Inert atmosphere
9.2: 0.5 h / 20 °C / Inert atmosphere
9.3: 3 h / Inert atmosphere
10.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / Inert atmosphere
11.1: hydrogen bromide / water / 10 h / Reflux
12.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C
References:
Ding, Rui;Fu, Jian-Guo;Xu, Guang-Qiang;Sun, Bing-Feng;Lin, Guo-Qiang [Journal of Organic Chemistry,2014,vol. 79,# 1,p. 240 - 250]
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