methyl (4R^*,5S^*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate

Base Information

• Chemical Name: methyl (4R^*,5S^*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate
• CAS No.: 102836-27-1
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.279
• Mol file: 102836-27-1.mol

Synonyms:methyl (4R^*,5S^*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate

Chemical Property of methyl (4R^*,5S^*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4R^*,5S^*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate

There total 9 articles about methyl (4R^*,5S^*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate 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: 77.0%

methyl 2-diazo-3-oxo-5-phenylheptanoate (104620-51-1) → methyl (4R*,5S*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate (102836-27-1)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane;

DOI:10.1021/ja00284a037

Reference yield: 66.0%

methyl 3-oxo-5-phenylheptanoate (102836-26-0) → methyl (4R*,5S*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate (102836-27-1)

Guidance literature:

With triethylamine; Methanesulfonyl azide; rhodium(II) acetate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)98618-0

Reference yield:

1-bromopropylbenzene (2114-36-5,101308-38-7) → methyl (4R*,5S*)-5-methyl-2-oxo-3-phenylcyclopentanecarboxylate (102836-27-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 29 percent / n-BuLi, diisopropylamine / tetrahydrofuran / -78 °C

2: 86 percent / methanesulfonyl azide, triethylamine / acetonitrile / 3 h / Ambient temperature

3: 77 percent / Rh₂(OAc)4 / CH₂Cl₂

With dirhodium tetraacetate; n-butyllithium; triethylamine; diisopropylamine; Methanesulfonyl azide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00284a037

upstream raw materials:

4-Methyl-3-phenyl-cyclopentanon

carbonic acid dimethyl ester

4-methyl-3-phenyl-2-cyclopentenone

4-methyl-1-phenyl-4-pentene-1-one

Downstream raw materials:

(3R,4R)-3-Methyl-4-phenyl-cyclopentanone