ChemicalBook CAS DataBase List Huperzine B

Huperzine B synthesis

13synthesis methods

Product Name:Huperzine B
CAS Number:103548-82-9
Molecular formula:C16H20N2O
Molecular Weight:256.34

89-82-7 Synthesis

89-82-7
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$12.00/250mg

103548-82-9
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$160.00/2.5mg

1H-5,10b-Propano-1,7-phenanthrolin-8(7H)-one, 2,3,4,4a,5,6,7-heptahydro-12-methyl-, (4aR,5S,10bR,12R)-

107965-41-3
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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