(1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

Base Information

Chemical Name:(1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline
CAS No.:257299-93-7
Molecular Formula:C₂₂H₃₉NO₃Si
Molecular Weight:393.642
Hs Code.:

Synonyms:(1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

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Chemical Property of (1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

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Technology Process of (1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

There total 1 articles about (1R,3S)-6,8-Dimethoxy-1-methyl-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: 85.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 257299-92-6
((1R,3S)-6,8-Dimethoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-methanol

: 257299-93-7
(1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

Guidance literature:: ((1R,3S)-6,8-Dimethoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-methanol; With sodium hydride; In tetrahydrofuran;

triisopropylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -78 ℃;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield: 93.0%

: 98-59-9
p-toluenesulfonyl chloride

: 257299-93-7
(1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

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

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

: 257299-93-7
(1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

: [(1R,3S)-5-(4-Benzyloxy-5-methoxy-7-triisopropylsilanyloxymethyl-naphthalen-1-yl)-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

Guidance literature:: Multi-step reaction with 6 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

4: 99 percent / DCC / CH₂Cl₂ / 14 h / 20 °C

5: 81 percent / K₃PO₄; 2,6-di-tert-butyl-4-methylphenol / [Pd(dppf)Cl₂] / dimethylformamide / 117 °C

6: 85 percent / NaOH; MeOH / 20 °C

With methanol; sodium hydroxide; potassium phosphate; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; iodine; triethylamine; dicyclohexyl-carbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Tosylation / 2: Iodination / 3: Desilylation / 4: Esterification / 5: Arylation / 6: Saponification;
DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W