ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.0^2,7]octane-1-carboxylate

Base Information

• Chemical Name: ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.0^2,7]octane-1-carboxylate
• CAS No.: 773080-83-4
• Molecular Formula: C₂₅H₃₁BrO₆
• Molecular Weight: 507.422

Synonyms:ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.0^2,7]octane-1-carboxylate

Chemical Property of ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.0^2,7]octane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.0^2,7]octane-1-carboxylate

There total 3 articles about ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.0^2,7]octane-1-carboxylate 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: 51.0%

ethyl (S,Z)-2-bromo-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-enoate (161792-18-3) + 2-(2-bromobenzyl)-3-ethoxycyclohex-2-en-1-one (773080-82-3) → ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.02,7]octane-1-carboxylate (773080-83-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -80 ℃; for 5h;

DOI:10.1016/j.tet.2004.06.094

Reference yield:

1,3-cylohexanedione (504-02-9) → ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.02,7]octane-1-carboxylate (773080-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / KOH / H₂O / 120 h / 20 °C / pH 12

2: 79 percent / CH₂Cl₂ / 3 h / 20 °C

3: 51 percent / LDA / tetrahydrofuran / 5 h / -80 °C

With potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tet.2004.06.094

Reference yield:

2-(2-bromobenzyl)-cyclohexane-1,3-dione (134079-02-0) → ethyl (1S,2R,5S,7S,8R,4'S)-7-(2-bromobenzyl)-8-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-ethoxy-6-oxotricyclo[3.2.1.02,7]octane-1-carboxylate (773080-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / CH₂Cl₂ / 3 h / 20 °C

2: 51 percent / LDA / tetrahydrofuran / 5 h / -80 °C

With lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2004.06.094

upstream raw materials:

ethyl (S,Z)-2-bromo-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-enoate

2-(2-bromobenzyl)-3-ethoxycyclohex-2-en-1-one

1,3-cylohexanedione

2-(2-bromobenzyl)-cyclohexane-1,3-dione

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