3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 441794-93-0
• Molecular Formula: C₂₃H₃₃NO₅
• Molecular Weight: 403.519

Synonyms:3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

There total 10 articles about 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 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:

p-methoxyphenyllithium (14774-77-7) → 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (441794-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / CuBr₂*Me₂S; BF₃*Et₂O / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 60 percent / LiCl; Hunig's base / acetonitrile

3.1: 90 percent / H₂ / Pd/C / ethyl acetate

4.1: NaBH₄ / methanol / 0 °C

4.2: 40 percent / pTSA / toluene / 5 h / Heating

With sodium tetrahydroborate; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; acetonitrile; 2.1: Horner-Emmons-Wadsworth reaction;

DOI:10.1021/jo011184i

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (441794-93-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 100 percent / LiHMDS / tetrahydrofuran / 4 h / -78 °C

2.1: 70 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

3.1: DIBAl-H / tetrahydrofuran / 2 h / -78 °C

4.1: 11.4 g / pTSA

5.1: 72 percent / MsCl; Et₃N; DMAP / CH₂Cl₂

6.1: 82 percent / H₂; NaHCO₃ / Pd/C / ethyl acetate

7.1: 70 percent / CuBr₂*Me₂S; BF₃*Et₂O / tetrahydrofuran; hexane / -78 - 20 °C

8.1: 60 percent / LiCl; Hunig's base / acetonitrile

9.1: 90 percent / H₂ / Pd/C / ethyl acetate

10.1: NaBH₄ / methanol / 0 °C

10.2: 40 percent / pTSA / toluene / 5 h / Heating

With 1H-imidazole; dmap; sodium tetrahydroborate; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile; 8.1: Horner-Emmons-Wadsworth reaction;

DOI:10.1021/jo011184i

Reference yield:

(2S,4S)-4-Isopropyl-5-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (441794-52-1) → 3S-isopropyl-2S-(4-methoxyphenyl)-5S-(5-oxotetrahydrofuran-2S-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (441794-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / CuBr₂*Me₂S; BF₃*Et₂O / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 60 percent / LiCl; Hunig's base / acetonitrile

3.1: 90 percent / H₂ / Pd/C / ethyl acetate

4.1: NaBH₄ / methanol / 0 °C

4.2: 40 percent / pTSA / toluene / 5 h / Heating

With sodium tetrahydroborate; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; acetonitrile; 2.1: Horner-Emmons-Wadsworth reaction;

DOI:10.1021/jo011184i

upstream raw materials:

p-methoxyphenyllithium

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

(2S,4S)-4-Isopropyl-5-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S,4S)-4-Isopropenyl-5-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Downstream raw materials:

5S-(4S-isopropenyl-5-oxotetrahydrofuran-2S-yl)-3S-isopropyl-2S-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

5S-[4S-(1-hydroxy-1-methylethyl)-5-oxotetrahydrofuran-2S-yl]-3S-isopropyl-2S-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

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