(6aR)-4,5,6,6a,7,8-Hexahydro-2,10,11,12-tetramethoxy-6-methylbenzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-ol

Base Information

Chemical Name:(6aR)-4,5,6,6a,7,8-Hexahydro-2,10,11,12-tetramethoxy-6-methylbenzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-ol
CAS No.:23117-57-9
Molecular Formula:C₂₂H₂₇NO₅
Molecular Weight:385.46
Hs Code.:
Mol file:23117-57-9.mol

Synonyms:Benzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-ol,4,5,6,6a,7,8-hexahydro-2,10,11,12-tetramethoxy-6-methyl-, (R)-; C-Homo-6ab-aporphin-1-ol,2,9,10,11-tetramethoxy- (8CI); Kreysigine (6CI); (-)-Kreysigine; Kreysigin

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (6aR)-4,5,6,6a,7,8-Hexahydro-2,10,11,12-tetramethoxy-6-methylbenzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-ol

Chemical Property:

Melting Point:187-8°C

Purity/Quality:: >95% by HPLC ^*data from raw suppliers

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General Description (6aR)-4,5,6,6a,7,8-Hexahydro-2,10,11,12-tetramethoxy-6-methylbenzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-ol, also known as kreysigine, is an aporphine alkaloid that can be efficiently synthesized via oxidative coupling using iron(III) chloride in dichloromethane, followed by reductive treatment with methanol, yielding the product in 71% yield. This method demonstrates a practical route for its preparation compared to alternative conditions or reagents.

Technology Process of (6aR)-4,5,6,6a,7,8-Hexahydro-2,10,11,12-tetramethoxy-6-methylbenzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-ol

There total 5 articles about (6aR)-4,5,6,6a,7,8-Hexahydro-2,10,11,12-tetramethoxy-6-methylbenzo[6,7]cyclohept[1,2,3-ij]isoquinolin-1-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: 41.0%

: 47764-93-2
1-(3',4',5'-trimethoxyphenethyl)-2-methyl-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline

: 31735-22-5,23117-57-9
(+/-)-Kreysigin

Guidance literature:: With boron trifluoride diethyl etherate; thallium(III) trifluoroacetate; In dichloromethane; trifluoroacetic acid; 1.) 0 deg C, 8 h, 2.) room temperature, 20 h;
DOI:10.1021/ja00541a021

Reference yield:

: 38726-41-9,38726-70-4
7-hydroxy-6-methoxy-1-(3',4',5'-trimethoxyphenethyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline

: 31735-22-5,23117-57-9
(+/-)-Kreysigin

Guidance literature:: With methanol; iron(III) chloride; Yield given. Multistep reaction; 1.) dichloromethane, 9 h; 2.) overnight;
DOI:10.1016/00404-0399(50)1037I-

Reference yield:

: 142542-98-1
merenderine N-oxide

: 26287-94-5,23117-57-9
kreysiginine

Guidance literature:: Multi-step reaction with 2 steps

1: 20percent HCl, zinc dust / 3 h

With hydrogenchloride; zinc;
DOI:10.1007/BF00629836