methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate
CAS No.:1418177-72-6
Molecular Formula:C₂₉H₃₁NO₄
Molecular Weight:457.569
Hs Code.:

Synonyms:methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

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Chemical Property of methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

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Technology Process of methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

There total 2 articles about methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-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: 28.0%

: 104-92-7
1-bromo-4-methoxy-benzene

: 1418177-70-4
methyl (2R)-1-(4,4-diphenylbut-3-en-1-yl)-4-oxopyrrolidine-2-carboxylate

: 1418177-72-6
methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

: 1418177-75-9
methyl (2R,4R)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

Guidance literature:: 1-bromo-4-methoxy-benzene; With magnesium; In tetrahydrofuran; for 0.666667h;

With cerium(III) chloride; In tetrahydrofuran; at 0 ℃; for 1h;

methyl (2R)-1-(4,4-diphenylbut-3-en-1-yl)-4-oxopyrrolidine-2-carboxylate; In tetrahydrofuran; at -60 ℃; for 20h; diastereoselective reaction;
DOI:10.1016/j.bmc.2012.11.015

Reference yield:

: 850741-33-2
methyl (2R,4R)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxypyrrolidine-2-carboxylate

: 1418177-72-6
methyl (2R,4S)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.17 h / -78 °C

1.2: 0.17 h / -78 - 20 °C

2.1: magnesium / tetrahydrofuran / 0.67 h

2.2: 1 h / 0 °C

2.3: 20 h / -60 °C

With oxalyl dichloride; magnesium; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1016/j.bmc.2012.11.015