1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

Base Information

Chemical Name:1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene
CAS No.:1385026-50-5
Molecular Formula:C₂₄H₂₇BrN₂O₄
Molecular Weight:487.393
Hs Code.:

Synonyms:1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

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Chemical Property of 1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

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Technology Process of 1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

There total 1 articles about 1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene 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:

: 1385026-33-4
1-tert-butoxycarbonylamino-4-bromo-5,6,8,9-tetrahydro-benzocyclohepten-7-one

: 501-53-1,94274-21-2
benzyl chloroformate

: 1385026-51-6
4-bromo-1-tertbutoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

: 1385026-50-5
1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

Guidance literature:: 1-tert-butoxycarbonylamino-4-bromo-5,6,8,9-tetrahydro-benzocyclohepten-7-one; With t-butyldimethylsiyl triflate; triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

benzyl chloroformate; regioselective reaction; Further stages;
DOI:10.1016/j.tet.2012.05.121

Reference yield: 80.0%

: 1385026-50-5
1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

: 4-bromo-1-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-5,6-epoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;
DOI:10.1016/j.tet.2012.05.121

Reference yield:

: 1385026-50-5
1-bromo-4-tert-butoxycarbonylamino-7-benzyloxycarbonylamino-6,7-dihydro-5H-benzocycloheptene

: 1338797-32-2
1-bromo-4-phenyl-7-tert-butyloxycarbonylamino-5,7,8,9-tetrahydro-benzocyclohepten-6-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / -78 - -30 °C

2.2: 0.5 h / -30 °C

3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 5 h / Inert atmosphere; Reflux

5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 20 h / 30 - 80 °C / Inert atmosphere

7.1: hydrogen bromide; acetic acid / 16 h / 20 °C

8.1: sodium carbonate / methanol / 1.5 h / 0 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; hydrogen bromide; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; copper(ll) bromide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; toluene; acetonitrile; 4.1: Suzuki coupling / 6.1: Sandmeyer reaction;
DOI:10.1016/j.tet.2012.05.121