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

Base Information

• Chemical Name: (6S,3aR,6aS,S_R)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one
• CAS No.: 861145-08-6
• Molecular Formula: C₂₁H₂₃NO₄S
• Molecular Weight: 385.484

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

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

Chemical Property:

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

There total 5 articles about (6S,3aR,6aS,S_R)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one 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: 86.0%

(2S,3S,4R,SR)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-07-5) → (6S,3aR,6aS,SR)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one (861145-08-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 3h;

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) → (6S,3aR,6aS,SR)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one (861145-08-6)

Guidance literature:

Multi-step reaction with 4 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

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; 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) → (6S,3aR,6aS,SR)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one (861145-08-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

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

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

DOI:10.1021/ol051003p

upstream raw materials:

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

(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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