Cyclopentanecarboxylic acid, 2-hydroxy-5-methyl-, methyl ester, (1R,2S,5S)-

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 2-hydroxy-5-methyl-, methyl ester, (1R,2S,5S)-
• CAS No.: 182683-23-4
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol file: 182683-23-4.mol

Synonyms:Cyclopentanecarboxylicacid, 2-hydroxy-5-methyl-, methyl ester, (1a,2a,5b)-

Chemical Property of Cyclopentanecarboxylic acid, 2-hydroxy-5-methyl-, methyl ester, (1R,2S,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopentanecarboxylic acid, 2-hydroxy-5-methyl-, methyl ester, (1R,2S,5S)-

There total 6 articles about Cyclopentanecarboxylic acid, 2-hydroxy-5-methyl-, methyl ester, (1R,2S,5S)- 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:

(1S,2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-cyclopentanecarboxylic acid methyl ester → (anti,syn) 2-hydroxy-5-methyl-cyclopentanecarboxylic acid methyl ester (182683-23-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1016/0040-4039(96)01386-X

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-cyclopent-1-enecarboxylic acid ethyl ester (182683-03-0) → (anti,syn) 2-hydroxy-5-methyl-cyclopentanecarboxylic acid methyl ester (182683-23-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiCuBr₂; trimethylsilyl chloride / tetrahydrofuran / 2 h / -35 °C

1.2: NH₄Cl / tetrahydrofuran; H₂O / -30 °C

2.1: 0.39 g / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0 - 20 °C

With chloro-trimethyl-silane; Br₂Cu^(1-)*Li⁽¹⁺⁾; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)00044-8

Reference yield:

5-hydroxycyclopent-1-enecarboxylic acid methyl ester (328239-96-9) → (anti,syn) 2-hydroxy-5-methyl-cyclopentanecarboxylic acid methyl ester (182683-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: LiCuBr₂; trimethylsilyl chloride / tetrahydrofuran / 2 h / -35 °C

2.2: NH₄Cl / tetrahydrofuran; H₂O / -30 °C

3.1: 0.39 g / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; chloro-trimethyl-silane; Br₂Cu^(1-)*Li⁽¹⁺⁾; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00044-8

upstream raw materials:

diazomethane

(1R,2R,6R)-2-Acetoxy-5-methyl-cyclopentan-1-carbonsaeure-methylester

furopelargone A

(1R,2R,3R)-1-Acetyl-2-carboxy-3-methyl-cyclopentan, 'Methyl-trans-cis-nepetonat'