(R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester

Base Information

• Chemical Name: (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester
• CAS No.: 1170145-18-2
• Molecular Formula: C₁₆H₁₈O₃
• Molecular Weight: 258.317
• Mol file: 1170145-18-2.mol

Synonyms:(R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester

Chemical Property of (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester

There total 2 articles about (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl 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: 93.0%

benzyl 2-acetylhept-6-ynoate (1092110-30-9) → (S)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester + (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester (1170145-18-2)

Guidance literature:

With ent-9-amino(9-deoxy)epi-hydroquinine; [silver(I)(acetonitrile)](bis(trifluoromethanesulfonyl)imide); trifluoroacetic acid; In methanol; at 0 ℃; enantioselective reaction;

DOI:10.1039/c7cc01807j

Reference yield:

benzyl acetoacetate (5396-89-4) → (S)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester + (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester (1170145-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride

2: lanthanum(III) isopropoxide; (S)-2-hydroxy-N-(1-(2-hydroxyphenylamino)-3,3-dimethyl-1-oxobutan-2-yl)benzamide; silver(I) acetate; triphenylphosphine / ethyl acetate / 12 h / 0 °C / Inert atmosphere

With lanthanum(III) isopropoxide; (S)-2-hydroxy-N-(1-(2-hydroxyphenylamino)-3,3-dimethyl-1-oxobutan-2-yl)benzamide; silver(I) acetate; sodium hydride; triphenylphosphine; In ethyl acetate; 2: Conia-ene reaction;

DOI:10.1002/anie.201102114

Reference yield:

p-bromophenylsulfonyl hydrazide (2297-64-5) + (R)-1-acetyl-2-methylene-cyclopentanecarboxylic acid benzyl ester (1170145-18-2) → C15H15BrN2O3S (1170145-43-3)

Guidance literature:

In benzene; for 72h; Reflux; Inert atmosphere;

DOI:10.1021/ja9004859

upstream raw materials:

benzyl 2-acetylhept-6-ynoate

benzyl acetoacetate

Downstream raw materials:

C₁₅H₁₅BrN₂O₃S