(2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid

Base Information

• Chemical Name: (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
• CAS No.: 90319-80-5
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 90319-80-5.mol

Synonyms:(2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid

Chemical Property of (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid

There total 41 articles about (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid 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: 76.0%

(2S)-2-<4-((1R)-2-oxocyclopentylmethyl)phenyl>propionic acid (83599-42-2) → (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid (90319-80-5,371753-20-7)

Guidance literature:

With Torulaspora delbrueckii NBRC 10921; In ethanol; at 30 ℃; optical yield given as %de; stereoselective reaction; Enzymatic reaction;

DOI:10.1016/j.tetasy.2011.06.019

Reference yield:

(R)-1-Amino-2-(methoxymethyl)pyrrolidine (72748-99-3,187035-29-6) → (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid (90319-80-5,371753-20-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / cyclohexane / Reflux

2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C

2.2: 2.5 h / -100 - -78 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 10 h / 20 °C

5.1: Torulaspora delbrueckii NBRC 10921 / ethanol / 30 °C / Enzymatic reaction

With dipyridinium dichromate; tetrabutyl ammonium fluoride; tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; cyclohexane; N,N-dimethyl-formamide; pentane;

DOI:10.1016/j.tetasy.2011.06.019

Reference yield:

(R)-1-Amino-2-(methoxymethyl)pyrrolidine (72748-99-3,187035-29-6) → (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid (90319-80-5,371753-20-7) + (2S)-2-<4-(trans-(1R,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid (83648-76-4,371753-20-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / cyclohexane / Reflux

2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C

2.2: 2.5 h / -100 - -78 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 10 h / 20 °C

5.1: Candida parapsilosis NBRC 1396 / ethanol / 30 °C / Enzymatic reaction

With dipyridinium dichromate; tetrabutyl ammonium fluoride; tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; cyclohexane; N,N-dimethyl-formamide; pentane;

DOI:10.1016/j.tetasy.2011.06.019

upstream raw materials:

loxoprofen

methyl (+/-)-2-<4-(trans-2-hydroxycyclopentylmethyl)phenyl>propionate

methyl (+/-)-2-<4-(cis-2-hydroxycyclopentylmethyl)phenyl>propionate

(2S)-2-<4-((1R)-2-oxocyclopentylmethyl)phenyl>propionic acid

Downstream raw materials:

2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionic acid

methyl (+/-)-2-<4-(cis-2-hydroxycyclopentylmethyl)phenyl>propionate

methyl (+/-)-2-<4-(trans-2-hydroxycyclopentylmethyl)phenyl>propionate

{2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid ethyl ester