(2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid

Base Information

• Chemical Name: (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid
• CAS No.: 14253-59-9
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Mol file: 14253-59-9.mol

Synonyms:

Chemical Property of (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid

There total 17 articles about (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid 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: 93.0%

methanol (67-56-1) + exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (14166-28-0) → (1R,2S,3R,4S)-2-(Methoxycarbonyl)bicyclo<2.2.1>heptane-3-carboxylic Acid (14253-59-9,55298-06-1,76232-01-4,116404-48-9,125226-86-0,128298-84-0,128441-83-8,130464-54-9,132747-52-5,135357-73-2)

Guidance literature:

With 4-((4-((1S)-hydroxy((2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-yl)oxy)butanoic acid modified Fe₃O₄ nanoparticles; In diethyl ether; at -45 ℃; for 60h; enantioselective reaction; Inert atmosphere;

DOI:10.1039/d1nj04081b

Reference yield:

dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1) → (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid (14253-59-9,55298-06-1,76232-01-4,116404-48-9,125226-86-0,128298-84-0,128441-83-8,130464-54-9,132747-52-5,135357-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 3 h / Ambient temperature; pig liver esterase (PLE), phosphate buffer, pH 7.8

2: H₂ / Pd/C / ethyl acetate

With hydrogen; palladium on activated charcoal; In ethyl acetate;

Reference yield:

(1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-((R)-methoxycarbonyl-phenyl-methyl) ester 3-methyl ester (130362-20-8) → (1S,2R,3S,4R)-2-(Methoxycarbonyl)-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid (14253-59-9,55298-06-1,76232-01-4,116404-48-9,125226-86-0,128298-84-0,128441-83-8,130464-54-9,132747-52-5,135357-73-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; Yield given;

DOI:10.1021/jo00013a009

upstream raw materials:

methanol

cis-5-norbornene-endo-2,3-dicarboxylic anhydride

Dimethyl norbornane-trans-2,3-dicarboxylate

(1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid

Refernces

• 1、 -. "Catalytic asymmetric desymmetrization of prochiral and meso compounds". Figure 4. . Retrieved 2008/06/13.
• 2、 Gastel, F. J. C. van,Klunder, A. J. H.,Zwanenburg, B.. "Enzymatic optical resolution of norbornanecarboxylic esters using Pig Liver Esterase". . p. 175 - 184. Retrieved 2007/10/02.