4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene

Base Information

• Chemical Name: 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene
• CAS No.: 141667-39-2
• Molecular Formula: C₂₁H₂₀N₂O₆S
• Molecular Weight: 428.466

Synonyms:4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene

Chemical Property of 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene

Chemical Property:

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Technology Process of 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene

There total 2 articles about 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene 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: 79.0%

1-nitroethylene (3638-64-0,26618-70-2) + 1-(4'-methylbenzenesulfonyl)-3-(phenylmethoxy)-2-pyridone (141667-30-3) → 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene (141667-39-2)

Guidance literature:

In dichloromethane; at 90 ℃; for 120h;

DOI:10.1021/jo00041a010

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene (141667-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) lithium hexamethyldisilazide / 1) THF, hexane, 0 deg C, 2) THF, hexane

2: 79 percent / CH₂Cl₂ / 120 h / 90 °C

With lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1021/jo00041a010

Reference yield: 89.0%

4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-endo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene (141667-39-2) → 4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-exo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene (141725-49-7)

Guidance literature:

With ammonium formate; In methanol; dichloromethane; for 60h; Ambient temperature;

DOI:10.1021/jo00041a010

upstream raw materials:

1-nitroethylene

1-(4'-methylbenzenesulfonyl)-3-(phenylmethoxy)-2-pyridone

p-toluenesulfonyl chloride

Downstream raw materials:

4-(benzyloxy)-2-(4'-methylbenzenesulfonyl)-5-exo-nitro-3-oxo-2-azabicyclo<2.2.2>-7-octene

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