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

Base Information

• Chemical Name: (1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline
• CAS No.: 257300-03-1
• Molecular Formula: C₂₉H₄₅NO₅SSi
• Molecular Weight: 547.832

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

There total 8 articles about (1R,3S)-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: 93.0%

p-toluenesulfonyl chloride (98-59-9) + (1R,3S)-6,8-Dimethoxy-1-methyl-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline (257299-93-7) → (1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline (257300-03-1)

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:

1-chloro-3,5-dimethoxybenzene (7051-16-3) → (1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline (257300-03-1)

Guidance literature:

Multi-step reaction with 8 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

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; trimethylaluminum; sodium hydride; magnesium; ethylene dibromide; triethylamine; triphenylphosphine; 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;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethylamine (228704-10-7) → (1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline (257300-03-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / NEt₃ / CH₂Cl₂ / 20 °C

2.1: 97 percent / POCl₃; 2,4,6-collidine / acetonitrile / 3 h / 85 °C

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

4.1: NaH / tetrahydrofuran

4.2: 85 percent / tetrahydrofuran / -78 °C

5.1: 93 percent / NEt₃ / CH₂Cl₂ / 20 °C

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; trimethylaluminum; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 1.1: Acetylation / 2.1: Bischler-Napieralski cyclization / 3.1: Reduction / 4.1: Metallation / 4.2: Etherification / 5.1: Tosylation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

upstream raw materials:

p-toluenesulfonyl chloride

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

1-chloro-3,5-dimethoxybenzene

2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethylamine

Downstream raw materials:

2-Diphenylphosphanyl-benzoic acid (1R,3S)-5-iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-ylmethyl ester

C₃₂H₃₃INO₅PS

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

(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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