benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate

Base Information

• Chemical Name: benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate
• CAS No.: 1372147-81-3
• Molecular Formula: C₂₇H₂₆BrNO₄
• Molecular Weight: 508.412

Synonyms:benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate

Chemical Property of benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate

Chemical Property:

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Technology Process of benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate

There total 5 articles about benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-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: 85.0%

1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine (1372147-73-3) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate (1372147-81-3)

Guidance literature:

With potassium hydrogencarbonate; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2012.03.005

Reference yield:

3-bromo-2-fluoro-phenol (156682-53-0) → benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate (1372147-81-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 4 h / Reflux

2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice

2.2: 2 h / 100 °C

3.1: acetone / 18 h / Reflux

4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C

5.1: potassium hydrogencarbonate / dichloromethane / 24 h / 0 - 20 °C

With sodium tetrahydroborate; sodium hydride; potassium carbonate; potassium hydrogencarbonate; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; acetone; mineral oil;

DOI:10.1016/j.tetlet.2012.03.005

Reference yield:

4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridine (1372147-59-5) → benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate (1372147-81-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetone / 18 h / Reflux

2: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C

3: potassium hydrogencarbonate / dichloromethane / 24 h / 0 - 20 °C

With sodium tetrahydroborate; potassium hydrogencarbonate; In methanol; dichloromethane; acetone;

DOI:10.1016/j.tetlet.2012.03.005

upstream raw materials:

3-bromo-2-fluoro-phenol

4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridine

1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridinium bromide

1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine

Downstream raw materials:

benzyl 7-(benzyloxy)-2',3'-dihydro-1'H,2H-spiro[1-benzofuran-3,4'-pyridine]-1'-carboxylate

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