[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

Base Information

Chemical Name:[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol
CAS No.:257299-95-9
Molecular Formula:C₂₀H₂₄INO₅S
Molecular Weight:517.385
Hs Code.:

Synonyms:[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

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Chemical Property of [(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

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Technology Process of [(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

There total 11 articles about [(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol 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: 99.0%

: 257299-94-8
(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

: 257299-95-9
[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

: 7051-16-3
1-chloro-3,5-dimethoxybenzene

: 257299-95-9
[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

Guidance literature:: Multi-step reaction with 10 steps

1.1: Mg; BrCH₂CH₂Br / tetrahydrofuran / 10 h / Heating

1.2: 92 percent / CuBr*SMe₂ / tetrahydrofuran / 4.5 h / -20 °C

2.1: 88 percent / PPh₃; DEAD / tetrahydrofuran / 20 h / 0 - 20 °C

3.1: 89 percent / H₂NNH₂ / ethanol / 7 h / Heating

4.1: 99 percent / NEt₃ / CH₂Cl₂ / 20 °C

5.1: 97 percent / POCl₃; 2,4,6-collidine / acetonitrile / 3 h / 85 °C

6.1: LiAlH₄; Me₃Al / tetrahydrofuran; hexane / -78 - 20 °C

7.1: NaH / tetrahydrofuran

7.2: 85 percent / tetrahydrofuran / -78 °C

8.1: 93 percent / NEt₃ / CH₂Cl₂ / 20 °C

9.1: 89 percent / I₂; PhI(O₂CCF₃)2 / CH₂Cl₂ / -10 - 0 °C

10.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; iodine; trimethylaluminum; sodium hydride; magnesium; ethylene dibromide; triethylamine; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; hydrazine; diethylazodicarboxylate; trichlorophosphate; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile; 1.1: Metallation / 1.2: Ring cleavage / 2.1: Mitsunobu reaction / 3.1: Hydrazinolysis / 4.1: Acetylation / 5.1: Bischler-Napieralski cyclization / 6.1: Reduction / 7.1: Metallation / 7.2: Etherification / 8.1: Tosylation / 9.1: Iodination / 10.1: Desilylation;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 257299-95-9
[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / NEt₃ / CH₂Cl₂ / 20 °C

2: 89 percent / I₂; PhI(O₂CCF₃)2 / CH₂Cl₂ / -10 - 0 °C

3: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With tetrabutyl ammonium fluoride; iodine; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; dichloromethane; 1: Tosylation / 2: Iodination / 3: Desilylation;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W