tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 1591920-21-6
• Molecular Formula: C₂₇H₂₈BrNO₂
• Molecular Weight: 478.429

Synonyms:tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

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Technology Process of tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 5 articles about tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-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: 90.0%

tert-butyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1381986-46-4) + 1-bromomethyl-4-bromobenzene (589-15-1) → tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1591920-21-6)

Guidance literature:

tert-butyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.0666667h;

1-bromomethyl-4-bromobenzene; In tetrahydrofuran; hexane; at 20 ℃; for 16h;

DOI:10.1021/ja500485f

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1591920-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 20 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.07 h / -50 °C

2.2: 16 h / 20 °C

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1021/ja500485f

Reference yield:

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → tert-butyl 1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1591920-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 20 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.07 h / -50 °C

2.2: 16 h / 20 °C

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1021/ja500485f

upstream raw materials:

di-tert-butyl dicarbonate

1-phenyl-1,2,3,4-tetrahydroisoquinoline

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

tert-butyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Downstream raw materials:

tert-butyl (1S)-1-(4-bromobenzyl)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

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