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

Base Information

• Chemical Name: (2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde
• CAS No.: 861145-12-2
• Molecular Formula: C₂₂H₂₅NO₄S
• Molecular Weight: 399.511

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

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

Chemical Property:

Purity/Quality:

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

There total 9 articles about (2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde 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%

1-[(3R,4S,5S)-5-(4-Methoxy-phenyl)-4-((E)-2-methoxy-vinyl)-1-((R)-toluene-4-sulfinyl)-pyrrolidin-3-yl]-ethanone → (2S,3S,4R,SR)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde (861145-12-2)

Guidance literature:

1-[(3R,4S,5S)-5-(4-Methoxy-phenyl)-4-((E)-2-methoxy-vinyl)-1-((R)-toluene-4-sulfinyl)-pyrrolidin-3-yl]-ethanone; With mercury(II) diacetate; In tetrahydrofuran; at -10 - 20 ℃;

With potassium iodide; In tetrahydrofuran;

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-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde (861145-12-2)

Guidance literature:

Multi-step reaction with 8 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

4.1: 86 percent / KOBu-t / tetrahydrofuran / 3 h / 0 °C

5.1: DIBAL-H / tetrahydrofuran; heptane / 4.5 h / -78 °C

6.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

6.2: 0.16844 g / tetrahydrofuran; toluene / 0 - 20 °C

7.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

8.1: Hg(OAc)2 / tetrahydrofuran / -10 - 20 °C

8.2: 91 percent / aq. KI / tetrahydrofuran

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; mercury(II) diacetate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; n-heptane; dichloromethane; 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-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde (861145-12-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / NaBr; TEMPO; NaOCl / NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

2.1: 99 percent / tetrahydrofuran / 5 h / -78 °C

3.1: 86 percent / KOBu-t / tetrahydrofuran / 3 h / 0 °C

4.1: DIBAL-H / tetrahydrofuran; heptane / 4.5 h / -78 °C

5.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

5.2: 0.16844 g / tetrahydrofuran; toluene / 0 - 20 °C

6.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

7.1: Hg(OAc)2 / tetrahydrofuran / -10 - 20 °C

7.2: 91 percent / aq. KI / tetrahydrofuran

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium tert-butylate; mercury(II) diacetate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; n-heptane; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/ol051003p

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

(2S,3S,4R,S_R)-4-formyl-2-(4-methoxyphenyl)-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:

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

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