(1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester

Base Information

• Chemical Name: (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester
• CAS No.: 700867-39-6
• Molecular Formula: C₁₅H₁₆N₂O₆
• Molecular Weight: 320.302

Synonyms:(1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester

Chemical Property of (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester

There total 1 articles about (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester 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: 86.0%

(1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-3-carboxylic acid (171754-03-3,171754-02-2) + 4-nitrobenzyl chloroformate (4457-32-3) → (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester (700867-39-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/j.tet.2004.01.102

Reference yield: 87.0%

2-amino-2,2-diphenylethan-1-ol (18903-44-1) + (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester (700867-39-6) → (1S,3R,4R)-3-(2'-hydroxy-1',1'-diphenylethylcarbamoyl)-2-azabicyclo[2.2.1]heptane-2-N-carboxylic acid p-nitrobenzyl ester (791613-40-6)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol048399+

Reference yield: 87.0%

D-2-phenylglycinol (56613-80-0) + (1S,3S,4R)-2-aza-bicyclo-[2.2.1]-heptane-2,3-dicarboxylic acid 2-p-nitrobenzyl ester (700867-39-6) → (1S,3R,4R)-3-(2'-hydroxy-1'(R)-phenyl-ethylcarbamoyl)-2-aza-bicyclo-[2.2.1]-heptane-2-N-carboxylic acid p-nitrobenzyl ester (700867-45-4)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2004.01.102

upstream raw materials:

(1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-3-carboxylic acid

4-nitrobenzyl chloroformate

Downstream raw materials:

(1S,3R,4R)-3-(2'-hydroxy-1'(S)-benzyl-ethylcarbamoyl)-2-aza-bicyclo-[2.2.1]-heptane-2-N-carboxylic acid p-nitrobenzyl ester

(1S,3R,4R)-3-(2'-hydroxy-1'(R)-benzyl-ethylcarbamoyl)-2-aza-bicyclo-[2.2.1]-heptane-2-N-carboxylic acid p-nitrobenzyl ester

(1S,3R,4R)-3-(2'-hydroxy-1'(R)-phenyl-ethylcarbamoyl)-2-aza-bicyclo-[2.2.1]-heptane-2-N-carboxylic acid p-nitrobenzyl ester

(1S,3R,4R)-3-(2'-hydroxy-1'(S)-phenyl-ethylcarbamoyl)-2-aza-bicyclo-[2.2.1]-heptane-2-N-carboxylic acid p-nitrobenzyl ester

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