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

Base Information

• Chemical Name: (1R,4S,5R,6S)-5,6-epoxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one
• CAS No.: 262280-37-5
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.278
• Mol file: 262280-37-5.mol

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

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

There total 3 articles about (1R,4S,5R,6S)-5,6-epoxy-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: 92.0%

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one (168960-17-6) → (1R,4S,5R,6S)-5,6-epoxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-37-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; for 8h; Heating;

DOI:10.1021/jm9904755

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (1R,4S,5R,6S)-5,6-epoxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / water / 1 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / Cooling with ice

2.2: 3 h / 0 - 20 °C

3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / Reflux; Inert atmosphere

With hydrogenchloride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.9b00672

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (1R,4S,5R,6S)-5,6-epoxy-2-(4'-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (262280-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / Cooling with ice

1.2: 3 h / 0 - 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / Reflux; Inert atmosphere

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.9b00672

upstream raw materials:

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

4-Methoxybenzyl alcohol

p-methoxybenzyl chloride

Downstream raw materials:

(1R,4R,5S,6S)-5-bromo-2-(4'-methoxybenzyl)-6-trimethylsiloxy-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

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

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