(1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one

Base Information

• Chemical Name: (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one
• CAS No.: 262280-42-2
• Molecular Formula: C₁₄H₁₅BrFNO₂
• Molecular Weight: 328.181
• Mol file: 262280-42-2.mol

Synonyms:(1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one

Chemical Property of (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one

There total 4 articles about (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one 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: 63.0%

(1S,4S,6S,7R)-6-bromo-7-hydroxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-38-6) → (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-42-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -80 - 20 ℃; for 10.5h;

DOI:10.1021/jm9904755

Reference yield:

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one (168960-17-6) → (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-42-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / m-chloroperbenzoic acid / CHCl₃ / 8 h / Heating

2.1: 48percent aq. HBr / acetonitrile / 6 h / 0 °C

2.2: 55 percent / 2,6-lutidine; DMAP / CH₂Cl₂

3.1: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

4.1: 63 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 10.5 h / -80 - 20 °C

With diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile; 1.1: Epoxidation / 2.1: Bromination / 2.2: Silylation / 3.1: Desilylation / 4.1: Fluorination;

DOI:10.1021/jm9904755

Reference yield:

(1R,4S,5R,6S)-5,6-epoxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-37-5) → (1S,4S,6S,7S)-6-bromo-7-fluoro-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-42-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 48percent aq. HBr / acetonitrile / 6 h / 0 °C

1.2: 55 percent / 2,6-lutidine; DMAP / CH₂Cl₂

2.1: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

3.1: 63 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 10.5 h / -80 - 20 °C

With diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; acetonitrile; 1.1: Bromination / 1.2: Silylation / 2.1: Desilylation / 3.1: Fluorination;

DOI:10.1021/jm9904755

upstream raw materials:

(1S,4S,6S,7R)-6-bromo-7-hydroxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

(1R,4S,5R,6S)-5,6-epoxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one

(1S,4S,6S,7R)-6-bromo-2-(4'-methoxybenzyl)-7-trimethylsiloxy-2-azabicyclo[2.2.1]heptan-3-one