Cyclopentanecarboxylic acid, 2-(4-fluorophenyl)-3-hydroxy-, methyl ester, (1R,2R,3S)-

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 2-(4-fluorophenyl)-3-hydroxy-, methyl ester, (1R,2R,3S)-
• CAS No.: 190269-75-1
• Molecular Formula: C13H15FO3
• Molecular Weight: 238.259
• Mol file: 190269-75-1.mol

Synonyms:

Chemical Property of Cyclopentanecarboxylic acid, 2-(4-fluorophenyl)-3-hydroxy-, methyl ester, (1R,2R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopentanecarboxylic acid, 2-(4-fluorophenyl)-3-hydroxy-, methyl ester, (1R,2R,3S)-

There total 11 articles about Cyclopentanecarboxylic acid, 2-(4-fluorophenyl)-3-hydroxy-, methyl ester, (1R,2R,3S)- 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:

methanol (67-56-1) + (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylic acid (190269-78-4) → methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate (190269-75-1)

Guidance literature:

With hydrogenchloride; for 1h; Heating;

DOI:10.1021/jo061268x

Reference yield:

3-hydroxy-2-cyclopenten-1-one (5870-62-2) → methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate (190269-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / potassium phosphate; palladium(II) acetate; 2-(di-tert-butylphosphino)biphenyl / dioxane / 12 h / Heating

2.1: phosphorus oxybromide; disodium hydrogenphosphate / acetonitrile / 1.5 h / 65 °C

2.2: potassium hydroxide / acetonitrile; H₂O / 20 °C

3.1: 90 percent / n-tributylamine / 5percent Pd/C / N,N-dimethyl-acetamide / 12 h / 60 °C / 517.16 Torr

4.1: (R)-1-CH₃-3,3-(C₆H₅)2-C₅H₇BNO; BH₃*SMe₃ / toluene / 2 h / -20 - -15 °C

4.2: Red-Al / toluene; tetrahydrofuran / 2.5 h / -40 - -25 °C

With potassium phosphate; disodium hydrogenphosphate; tributyl-amine; dimethylsulfide borane complex; (R)-1-CH₃-3,3-(C₆H₅)2-C₅H₇BNO; palladium diacetate; johnphos; phosphorus(V) oxybromide; 5percent Pd/C; In 1,4-dioxane; N,N-dimethyl acetamide; toluene; acetonitrile;

DOI:10.1021/jo025883m

Reference yield:

2-(4-fluorophenyl)-1,3-cyclopentanedione (379679-70-6) → methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate (190269-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: phosphorus oxybromide; disodium hydrogenphosphate / acetonitrile / 1.5 h / 65 °C

1.2: potassium hydroxide / acetonitrile; H₂O / 20 °C

2.1: 90 percent / n-tributylamine / 5percent Pd/C / N,N-dimethyl-acetamide / 12 h / 60 °C / 517.16 Torr

3.1: (R)-1-CH₃-3,3-(C₆H₅)2-C₅H₇BNO; BH₃*SMe₃ / toluene / 2 h / -20 - -15 °C

3.2: Red-Al / toluene; tetrahydrofuran / 2.5 h / -40 - -25 °C

With disodium hydrogenphosphate; tributyl-amine; dimethylsulfide borane complex; (R)-1-CH₃-3,3-(C₆H₅)2-C₅H₇BNO; phosphorus(V) oxybromide; 5percent Pd/C; In N,N-dimethyl acetamide; toluene; acetonitrile;

DOI:10.1021/jo025883m

upstream raw materials:

methyl 2-(4-fluorophenyl)-3-oxo-1-cyclopent-1-enecarboxylate

methanol

(1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylic acid

3-hydroxy-2-cyclopenten-1-one

Downstream raw materials:

(1R,2R,3S)-2-(4-Fluoro-phenyl)-3-trimethylsilanyloxy-cyclopentanecarboxylic acid methyl ester

(1R,2R,3S)-3[(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-2-(4-fluorophenyl)cyclopentane-1-carboxylic acid methyl ester

trichloroacetamide

3,5-bis(trifluoromethyl)styrene