(1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

Base Information

Chemical Name:(1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol
CAS No.:1354006-14-6
Molecular Formula:C₁₉H₂₉NO₄
Molecular Weight:335.444
Hs Code.:

Synonyms:(1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

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Chemical Property of (1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

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Technology Process of (1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

There total 10 articles about (1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

: 1354006-34-0
(1S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

: 1354006-14-6
(1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

Guidance literature:: With lithium hydroxide monohydrate; water; In ethanol; for 5h; Inert atmosphere; Reflux;
DOI:10.1016/j.tet.2011.11.031

Reference yield:

: 1354006-04-4
(3S,4R)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-1-cyclohexyl-6,7-dimethoxy-3,4-dihydroisoquinoline

: 1354006-14-6
(1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: dichloromethane / 40 h / 35 °C / Inert atmosphere

2: sodium tris(acetoxy)borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

3: lithium hydroxide monohydrate; water / ethanol / 5 h / Inert atmosphere; Reflux

With lithium hydroxide monohydrate; water; sodium tris(acetoxy)borohydride; In methanol; ethanol; dichloromethane;
DOI:10.1016/j.tet.2011.11.031

Reference yield:

: 1354006-46-4
C₁₉H₂₅NO₄

: 1354006-14-6
(1S,3S,4R)-1-cyclohexyl-3-(hydroxymethyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol

Guidance literature:: Multi-step reaction with 7 steps

1: dmap; triethylamine / dichloromethane / 20 h / 0 °C / Reflux; Inert atmosphere

2: hydrogen; palladium(II) hydroxide / 3 h / 760.05 Torr

3: sodium hydroxide / tetrahydrofuran; water / 0.08 h / 0 °C / Inert atmosphere

4: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C / Inert atmosphere

5: dichloromethane / 40 h / 35 °C / Inert atmosphere

6: sodium tris(acetoxy)borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

7: lithium hydroxide monohydrate; water / ethanol / 5 h / Inert atmosphere; Reflux

With 2-chloropyridine; dmap; lithium hydroxide monohydrate; trifluoromethylsulfonic anhydride; water; hydrogen; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 4: Bischler-Napieralski reaction;
DOI:10.1016/j.tet.2011.11.031