(1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester

Base Information

• Chemical Name: (1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester
• CAS No.: 119945-34-5
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• Mol file: 119945-34-5.mol

Synonyms:(1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester

Chemical Property of (1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester

There total 3 articles about (1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) 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:

(+)-Dimenthyl (1R,2R)-cyclopentane-1,2-dicarboxylate (96149-02-9) → (1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester (119945-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / KOH, 30percent aq. H₂O₂ / methanol / 14 h / 50 °C

2: 1.) LDA, 2.) HMPA / 1.) THF, -20 deg C, 1 h, 2.) THF, from -78 to -20 deg C, 5.5 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; dihydrogen peroxide; lithium diisopropyl amide; In methanol;

DOI:10.1021/ja00061a003

Reference yield:

(+)-Dimenthyl (1R,2R)-cyclopentane-1,2-dicarboxylate (96149-02-9) → (R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester (119909-63-6,119945-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH, 30percent H₂O₂ / methanol / 14 h / 50 °C

2: 1.) LDA / 1.) THF, -25 deg C, 1 h, 2.) 23 deg C, 16 h

With potassium hydroxide; dihydrogen peroxide; lithium diisopropyl amide; In methanol;

DOI:10.1021/ja00188a054

Reference yield:

2-methyl-3-bromo-1-propene (1458-98-6) + (1R,2R)-cyclopentane-1,2-dicarboxylic acid mono-(+)-menthyl ester (119909-62-5) → (1S,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester (119909-63-6) + (1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester (119945-34-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -20 deg C, 1 h, 2.) THF, from -78 to -20 deg C, 5.5 h;

DOI:10.1021/ja00061a003

upstream raw materials:

2-methyl-3-bromo-1-propene

(1R,2R)-cyclopentane-1,2-dicarboxylic acid mono-(+)-menthyl ester

(+)-Dimenthyl (1R,2R)-cyclopentane-1,2-dicarboxylate

Downstream raw materials:

(3aR,7aS)-5-Methyl-7-oxo-1,2,3,4,7,7a-hexahydro-indene-3a-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

(1S,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester 2-methyl ester

(1R,2R)-1-(2-Methyl-allyl)-cyclopentane-1,2-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester 2-methyl ester

(3aS,7aR)-5-Methyl-7-oxo-1,2,3,4,7,7a-hexahydro-indene-3a-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester