Cyclobutanecarboxylic acid, 2-methyl-, methyl ester, (1R,2R)-rel- (9CI)

Base Information

• Chemical Name: Cyclobutanecarboxylic acid, 2-methyl-, methyl ester, (1R,2R)-rel- (9CI)
• CAS No.: 57705-62-1
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.171
• Mol file: 57705-62-1.mol

Synonyms:Cyclobutanecarboxylic acid, 2-methyl-, methyl ester, (1R,2R)-rel- (9CI)

Chemical Property of Cyclobutanecarboxylic acid, 2-methyl-, methyl ester, (1R,2R)-rel- (9CI)

Chemical Property:

• PSA: 26.30000
• LogP: 1.20550

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclobutanecarboxylic acid, 2-methyl-, methyl ester, (1R,2R)-rel- (9CI)

There total 8 articles about Cyclobutanecarboxylic acid, 2-methyl-, methyl ester, (1R,2R)-rel- (9CI) 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: 68.0%

(+/-)-cis-1-carbomethoxy-2-bromomethyl-cyclobutane (134785-24-3,134930-17-9) → (+/-)-cis-1-carbomethoxy-2-methylcyclobutane (7687-35-6,14132-44-6,57705-62-1,134785-21-0,134877-07-9,134877-12-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In hexane;

DOI:10.1016/S0957-4166(00)82360-5

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + cis-1,2-cyclobutane dicarboxylic anhydride (4462-96-8) → (+/-)-cis-1-carbomethoxy-2-methylcyclobutane (7687-35-6,14132-44-6,57705-62-1,134785-21-0,134877-07-9,134877-12-6)

Guidance literature:

Multistep reaction; (i) H₂, Pt, (ii) /BRN= 102415/;

DOI:10.1021/jo01279a013

Reference yield:

cis-3-cyclobutene-1,2-dicarboxylic anhydride → (+/-)-cis-1-carbomethoxy-2-methylcyclobutane (7687-35-6,14132-44-6,57705-62-1,134785-21-0,134877-07-9,134877-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / NaBH₄ / tetrahydrofuran

2: 89 percent / H₂ / Pd/C / diethyl ether / 4 h

3: HBr / -78 - 20 °C

4: 0.67 g / NaBH₄ / hexamethylphosphoric acid triamide / 3 h / 0 - 20 °C

With sodium tetrahydroborate; hydrogen bromide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; 1: Reduction / 2: Catalytic hydrogenation / 3: Ring cleavage / 4: Reduction;

DOI:10.1021/jo0009550

upstream raw materials:

(+/-)-cis-1-carbomethoxy-2-bromomethyl-cyclobutane

2-Methyl-cyclobut-1-en-1-carbonsaeuremethylester

diazomethane

cis-1,2-cyclobutane dicarboxylic anhydride

Downstream raw materials:

(+)-(1S,2R)-1-carbomethoxy-2-methylcyclobutane

N-[(R)-α-(hydroxymethyl)benzyl]-(1R,2S)-cis-2-methylcyclobutanecarboxamide

(1S,2R)-2-Methyl-cyclobutanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide

cis-2-methylcyclobutanecarboxylic acid

Refernces

• 1、 Toone,Jones. "Enzymes in organic synthesis 49. Resolutions of racemic monocyclic esters with pig liver esterase". . p. 207 - 222. Retrieved 2007/10/02.