(2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

Base Information

• Chemical Name: (2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide
• CAS No.: 861145-05-3
• Molecular Formula: C₃₂H₃₂N₂O₄S
• Molecular Weight: 540.683

Synonyms:(2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

Chemical Property of (2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

There total 3 articles about (2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 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: 91.0%

(2S,3S,SR)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-04-2) → (2S,3S,4R,SR)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-05-3)

Guidance literature:

(2S,3S,S_R)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 50 ℃; for 2.25h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at -20 - 20 ℃;

DOI:10.1021/ol051003p

Reference yield:

(R)-(-)-N-(4-methoxybenzylidene)-p-toluenesulfonamide (929274-19-1) → (2S,3S,4R,SR)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / MgI₂ / tetrahydrofuran / 7 h / Heating

2.1: 9-BBN (dimer) / tetrahydrofuran / 2.25 h / 50 °C

2.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -20 - 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; magnesium iodide; In tetrahydrofuran;

DOI:10.1021/ol051003p

Reference yield:

2-methylene-cyclopropanecarboxylic acid diphenyl amide (440084-59-3) → (2S,3S,4R,SR)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / MgI₂ / tetrahydrofuran / 7 h / Heating

2.1: 9-BBN (dimer) / tetrahydrofuran / 2.25 h / 50 °C

2.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -20 - 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; magnesium iodide; In tetrahydrofuran;

DOI:10.1021/ol051003p

upstream raw materials:

(2S,3S,S_R)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

(R)-(-)-N-(4-methoxybenzylidene)-p-toluenesulfonamide

2-methylene-cyclopropanecarboxylic acid diphenyl amide

Downstream raw materials:

methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

(2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

(-)-kainic acid

(2S,3S,4R,S_R)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

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