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

Base Information

• Chemical Name: (2S,3S,4R,S_R)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide
• CAS No.: 861145-07-5
• Molecular Formula: C₃₃H₃₄N₂O₄S
• Molecular Weight: 554.71

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

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

Chemical Property:

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

There total 5 articles about (2S,3S,4R,S_R)-4-(1-hydroxyethyl)-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: 99.0%

(2S,3S,4R,SR)-4-formyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-06-4) + methylmagnesium bromide (75-16-1) → (2S,3S,4R,SR)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-07-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1021/ol051003p

Reference yield:

(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-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-07-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 9-BBN (dimer) / tetrahydrofuran / 2.25 h / 50 °C

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -20 - 20 °C

2.1: 91 percent / NaBr; TEMPO; NaOCl / NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

3.1: 99 percent / tetrahydrofuran / 5 h / -78 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; water; ethyl acetate; toluene;

DOI:10.1021/ol051003p

Reference yield:

(2S,3S,4R,SR)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-05-3) → (2S,3S,4R,SR)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaBr; TEMPO; NaOCl / NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

2: 99 percent / tetrahydrofuran / 5 h / -78 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; water; ethyl acetate; toluene;

DOI:10.1021/ol051003p

upstream raw materials:

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

methylmagnesium bromide

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

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

Downstream raw materials:

(6S,3aR,6aS,S_R)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one

(2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde

(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

(2S,3R,4S)-4-acetyl-3-methoxycarbonylmethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

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