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

Base Information

Chemical Name:(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline
CAS No.:257299-94-8
Molecular Formula:C₂₉H₄₄INO₅SSi
Molecular Weight:673.728
Hs Code.:

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

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Chemical Property of (1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

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Technology Process of (1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

There total 10 articles about (1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline 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: 89.0%

: 257300-03-1
(1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

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

Guidance literature:: With iodine; bis-[(trifluoroacetoxy)iodo]benzene; In dichloromethane; at -10 - 0 ℃;
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

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

Guidance literature:: Multi-step reaction with 9 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

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; 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;
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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / NEt₃ / CH₂Cl₂ / 20 °C

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

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