5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 441794-79-2
• Molecular Formula: C₂₃H₃₆NO₇P
• Molecular Weight: 469.515

Synonyms:5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

There total 9 articles about 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)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: 88.0%

dimethyl methane phosphonate (756-79-6) + 4S-isopropyl-5R-(4-methoxyphenyl)pyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester (441794-60-1) → 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (441794-79-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

DOI:10.1021/jo011184i

Reference yield:

1-bromo-4-methoxy-benzene (104-92-7) → 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (441794-79-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 46 percent / CuBr₂*Me₂S; BF₃*Et₂O; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2: 81 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 20 °C

3: 90 percent / H₂ / Pd/C / ethyl acetate / 24 h / 2068.65 Torr

4: 88 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

With dmap; n-butyllithium; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/jo011184i

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → 5S-[2-(dimethoxyphosphoryl)acetyl]-3S-isopropyl-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (441794-79-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / LiHMDS / tetrahydrofuran / 4 h / -78 °C

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

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

4: 11.4 g / pTSA

5: 46 percent / CuBr₂*Me₂S; BF₃*Et₂O; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

6: 81 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 20 °C

7: 90 percent / H₂ / Pd/C / ethyl acetate / 24 h / 2068.65 Torr

8: 88 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

With 1H-imidazole; dmap; n-butyllithium; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/jo011184i

upstream raw materials:

dimethyl methane phosphonate

4S-isopropyl-5R-(4-methoxyphenyl)pyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

1-bromo-4-methoxy-benzene

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

Downstream raw materials:

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

(2R,3S,5S)-3-Isopropyl-5-(3-methoxycarbonyl-propionyl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2R,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-2R-(4-methoxyphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

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