ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

Base Information

• Chemical Name: ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate
• CAS No.: 178739-03-2
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417

Synonyms:ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

Chemical Property of ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

Chemical Property:

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Technology Process of ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

There total 26 articles about ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate 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%

(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid (209214-30-2) → ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate (178739-03-2,173864-47-6)

Guidance literature:

With hydrogenchloride; ethanol; at 54 ℃; for 19h;

DOI:10.1021/jm9505369

Reference yield: 73.0%

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (624736-79-4) → ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate (178739-03-2,173864-47-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/ejoc.200300234

Reference yield:

ethyl (3S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)-3,4-dihydro-2H-pyrrole-4-carboxylate → ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate (178739-03-2,173864-47-6) + ethyl (2R,3S,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate (173864-47-6)

Guidance literature:

With hydrogen; Ni-Ra; In ethanol; at 50 ℃; for 40h; under 4560.31 Torr; Title compound not separated from byproducts.;

DOI:10.1021/jo000206i

upstream raw materials:

(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

ethyl trans-trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate

ethanol

ethyl (2R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

Downstream raw materials:

(2R,3R,4S)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-1-(N,N-di(n-butyl)aminocarbonylmethyl)pyrrolidine-3-carboxylic acid ethyl ester

ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+) mandelate

atrasentan

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-1-[(2,6-diethyl-phenylcarbamoyl)-methyl]-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

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