(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

Chemical Name:(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
CAS No.:1344118-38-2
Molecular Formula:C₂₉H₄₅NO₄Si
Molecular Weight:499.766
Hs Code.:

Synonyms:(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

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Chemical Property of (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

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Technology Process of (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

There total 4 articles about (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 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%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1344118-30-4
(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

: 1344118-38-2
(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: formaldehyd; (S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/jo201871c

Reference yield:

: 1344118-32-6
4-methoxy-3-(triisopropylsilanyloxy)benzyl bromide

: 1344118-38-2
(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.07 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; formic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

3.1: methanol / 0.5 h / 20 °C / Inert atmosphere

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With formic acid; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; potassium hexamethylsilazane; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 2.1: Noyori assymmetric transfer hydrogenation reaction;
DOI:10.1021/jo201871c

Reference yield:

: 1344118-29-1
1-(4-methoxy-3-triisopropylsilyloxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

: 1344118-38-2
(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 2 steps

1.1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; formic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

2.1: methanol / 0.5 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With formic acid; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; In methanol; N,N-dimethyl-formamide; 1.1: Noyori assymmetric transfer hydrogenation reaction;
DOI:10.1021/jo201871c