(2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Base Information

• Chemical Name: (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester
• CAS No.: 886116-88-7
• Molecular Formula: C₂₅H₃₃FN₂O₄
• Molecular Weight: 444.546
• Mol file: 886116-88-7.mol

Synonyms:

Chemical Property of (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

There total 4 articles about (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) 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:

{[1-(4-Cyano-phenyl)-meth-(Z)-ylidene]-amino}-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester + (E)-ethyl 3-fluoro-2-propenoate (131981-92-5) → (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (886116-88-7) + (2R,3S,4S,5R)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (886116-90-1)

Guidance literature:

With silver(I) acetate; triethylamine; In toluene; at -40 ℃; for 6h;

DOI:10.1055/s-2006-933127

Reference yield:

(-)-menthol (2216-51-5) → (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (886116-88-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.17 h

1.2: 86 percent / DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 100 percent / TFA / CH₂Cl₂ / 0.58 h / 20 °C

3.1: 90 percent / Na₂SO₄; Et₃N / 24 h / 20 °C

4.1: AgOAc; Et₃N / toluene / 6 h / -40 °C

With silver(I) acetate; sodium sulfate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1055/s-2006-933127

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-aminoacetate (63254-60-4,80655-94-3,120143-37-5) → (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (886116-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Na₂SO₄; Et₃N / 24 h / 20 °C

2: AgOAc; Et₃N / toluene / 6 h / -40 °C

With silver(I) acetate; sodium sulfate; triethylamine; In toluene;

DOI:10.1055/s-2006-933127

upstream raw materials:

(E)-ethyl 3-fluoro-2-propenoate

(-)-menthol

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-aminoacetate

(1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate