ChemicalBook CAS DataBase List ARMEPAVINE

ARMEPAVINE synthesis

8synthesis methods

Product Name:ARMEPAVINE
CAS Number:524-20-9
Molecular formula:C19H23NO3
Molecular Weight:313.39

14199-15-6 Synthesis

14199-15-6
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4-[[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol

14400-96-5
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524-20-9
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3423-02-7
1 suppliers
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5701-00-8
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Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: tetrabutyl-ammonium chloride; hydrogenchloride / water; acetonitrile / Electrochemical reaction
2.1: Electrochemical reaction
3.1: Electrochemical reaction
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C
5.1: 5%-palladium/activated carbon; hydrogen / methanol / 24 h / 20 °C
6.1: sodium hydroxide / methanol; water / 17 h / 0 °C
7.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C
8.1: trichlorophosphate / toluene / 16 h / Reflux
8.2: 6 h / -78 °C
9.1: hydrogen; palladium(II) hydroxide / ethyl acetate; methanol; water / 23 h / 20 °C
10.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C

References:

Kawabata, Yuki;Naito, Yu;Saitoh, Tsuyoshi;Kawa, Kohei;Fuchigami, Toshio;Nishiyama, Shigeru [European Journal of Organic Chemistry,2014,vol. 2014,# 1,p. 99 - 104]