(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

Chemical Name:(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
CAS No.:1354006-39-5
Molecular Formula:C₃₁H₅₀BrNO₄Si₂
Molecular Weight:636.817
Hs Code.:

(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Synonyms:(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Chemical Property of (1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Technology Process of (1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

There total 8 articles about (1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-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: 87.0%

: 1354006-09-9
(3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsi lyloxy)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline

: 1354006-39-5
(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

: (1R,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.11.031

Reference yield:

: 1354006-20-4
(S)-(3,4-dimethoxyphenyl)[(R)-1-(1-phenylethyl)aziridin-2-yl]methanone

: 1354006-39-5
(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 7 steps

1.1: zinc(II) chloride / methanol / 0.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: acetic acid / dichloromethane / 8 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

2.3: 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 20 h / 0 °C / Reflux; Inert atmosphere

4.1: hydrogen; palladium(II) hydroxide / 3 h / 760.05 Torr

5.1: sodium hydroxide / tetrahydrofuran; water / 0.08 h / 0 °C / Inert atmosphere

6.1: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C / Inert atmosphere

7.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

With 2-chloropyridine; dmap; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; hydrogen; palladium(II) hydroxide; acetic acid; triethylamine; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; 6.1: Bischler-Napieralski reaction;
DOI:10.1016/j.tet.2011.11.031

Reference yield:

: 1354006-46-4
C₁₉H₂₅NO₄

: 1354006-39-5
(1S,3S,4R)-1-(2-bromobenzyl)-4-(tert-butyldimethylsilyloxy)-3[(tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 5 steps

1: dmap; triethylamine / dichloromethane / 20 h / 0 °C / Reflux; Inert atmosphere

2: hydrogen; palladium(II) hydroxide / 3 h / 760.05 Torr

3: sodium hydroxide / tetrahydrofuran; water / 0.08 h / 0 °C / Inert atmosphere

4: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 0 °C / Inert atmosphere

5: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

With 2-chloropyridine; dmap; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; hydrogen; palladium(II) hydroxide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 4: Bischler-Napieralski reaction;
DOI:10.1016/j.tet.2011.11.031