Cyclopentanecarboxylic acid, 3-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 3-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]-, 1,1-dimethylethyl ester
• CAS No.: 646518-07-2
• Molecular Formula: C₁₈H₂₆O₅S
• Molecular Weight: 354.467
• Mol file: 646518-07-2.mol

Synonyms:

Chemical Property of Cyclopentanecarboxylic acid, 3-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopentanecarboxylic acid, 3-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]-, 1,1-dimethylethyl ester

There total 4 articles about Cyclopentanecarboxylic acid, 3-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]-, 1,1-dimethylethyl 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:

tert-butyl 3-methyl-2-oxocyclopentane-1-carboxylate (479201-46-2) → tert-butyl 3-methyl-2-(4-methylbenzenesulfonyloxy)cyclopentane-1-carboxylate (646518-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaBH₄ / ethanol / 0.75 h / 0 °C

2: pyridine / 0 °C

With pyridine; sodium tetrahydroborate; In ethanol;

DOI:10.1039/b306935b

Reference yield:

di-tert-butyl 1,6-hexanedioate (20270-53-5) → tert-butyl 3-methyl-2-(4-methylbenzenesulfonyloxy)cyclopentane-1-carboxylate (646518-07-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH; t-BuOH / toluene / Heating

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 91 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

3.1: 91 percent / NaBH₄ / ethanol / 0.75 h / 0 °C

4.1: pyridine / 0 °C

With pyridine; sodium tetrahydroborate; sodium hydride; tert-butyl alcohol; In tetrahydrofuran; ethanol; toluene; 1.1: Dieckmann cyclisation;

DOI:10.1039/b306935b

Reference yield:

tert-butyl 2-oxocyclopentanecarboxylate (84109-76-2) → tert-butyl 3-methyl-2-(4-methylbenzenesulfonyloxy)cyclopentane-1-carboxylate (646518-07-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 91 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.1: 91 percent / NaBH₄ / ethanol / 0.75 h / 0 °C

3.1: pyridine / 0 °C

With pyridine; sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; ethanol;

DOI:10.1039/b306935b

upstream raw materials:

p-toluenesulfonyl chloride

tert-butyl 2-hydroxy-3-methylcyclopentane-1-carboxylate

di-tert-butyl 1,6-hexanedioate

tert-butyl 2-oxocyclopentanecarboxylate

Downstream raw materials:

(1R,2S,3R)-3-methyl-2-aminocyclopentane carboxylic acid

Refernces

• 1、 Bailey, Simon,Davies, Stephen G.,Smith, Andrew D.,Withey, Jonathan M.. "Asymmetric synthesis of (1R,2S,3R)-γ-methyl-cis-pentacin by a kinetic resolution protocol". . p. 2910 - 2911. Retrieved 2007/10/03.