(R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester

Base Information

• Chemical Name: (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester
• CAS No.: 64471-47-2
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 64471-47-2.mol

Synonyms:(R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester

Chemical Property of (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

(R)-Methyl2-cyclopentyl-2-hydroxy-2-phenylacetate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester

There total 12 articles about (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl 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: 95.9%

methanol (67-56-1) + (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid (64471-45-0) → (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester (64471-47-2)

Guidance literature:

With sulfuric acid; for 24h; Reflux; Large scale;

Reference yield: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid (64471-45-0) → (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester (64471-47-2)

Guidance literature:

In diethyl ether; at 20 ℃; for 0.5h;

DOI:10.1080/00397910600602453

Reference yield:

(R)-Mandelic Acid (611-71-2) → (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester (64471-47-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / trifluoromethanesulfonic acid / pentane / 6 h / Heating

2.1: lithium bis(trimethylsilyl) amide / tetrahydrofuran; hexane / 1 h / cooling

2.2: 67 percent / tetrahydrofuran; hexane / 3 h

3.1: thionyl chloride; pyridine / tetrahydrofuran / 3 h / 0 °C

4.1: 87 percent / hydrogen / Pd/C / methanol / 10 h / 760 Torr

5.1: KOH / methanol; H₂O / 3 h / Heating

6.1: 95 percent / diethyl ether / 0.5 h / 20 °C

With pyridine; potassium hydroxide; thionyl chloride; trifluorormethanesulfonic acid; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; water; pentane;

DOI:10.1080/00397910600602453

upstream raw materials:

diazomethane

(2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid

(2R,5S)-2-(tert-butyl)-5-phenyl-5-(cyclopent-1-enyl)-1,3-dioxolan-4-one

(2R,5S)-2-(tert-butyl)-5-phenyl-5-(1-hydroxycyclopentyl)-1,3-dioxolan-4-one

Downstream raw materials:

(1R,2S)-2-((R)-2'-cyclopentyl-2'-hydroxy-2'-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo [2.2.1]heptane bromide

(1R,2S)-2-((R)-2'-cyclopentyl-2'-hydroxy-2'-phenylacetoxy)-7-methyl-7-azabicyclo[2.2.1]heptane

C₁₉H₂₅NO₃

(1R,2S)-2-((R)-2'-cyclopentyl-2'-hydroxy-2'-phenylacetoxy)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane

Refernces

• 1、 Malmquist, Jonas,Varn?s, Katarina,Svedberg, Marie,Vallée, Frédéric,Albert, Jeffrey S.,Finnema, Sjoerd J.,Schou, Magnus. "Discovery of a Novel Muscarinic Receptor PET Radioligand with Rapid Kinetics in the Monkey Brain". . p. 224 - 229. Retrieved 2018/03/01.
• 2、 Liu, Yan-Qing,Liu, He,Zhong, Bo-Hua,Deng, Yu-Lin,Liu, Ke-Liang. "Optical resolution, stereoselective synthesis, and crystal structure of 9α-(3-azabicyclo[3,3,1]nonanyl)-2′cyclopentyl-2′-hydroxy- 2′-phenylacetate". . p. 1403 - 1412. Retrieved 2007/10/03.