(+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

Base Information

• Chemical Name: (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester
• CAS No.: 613669-95-7
• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.349
• Mol file: 613669-95-7.mol

Synonyms:(+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

Chemical Property of (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

There total 6 articles about (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl 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: 91.0%

(1S,2S,4R)-4-Acetoxy-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (613669-91-3) → (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (613669-95-7)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃; for 12h;

DOI:10.1016/S0957-4166(03)00445-2

Reference yield: 39.0%

vinyl acetate (108-05-4,9003-20-7) + 4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester → (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (613669-95-7) + (-)-(1R,2R,4S)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (613669-92-4) + (1S,2S,4R)-4-Acetoxy-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (613669-91-3)

Guidance literature:

With Candida antarctica B lipase; at 20 ℃; for 3h; Enzymatic reaction;

DOI:10.1016/S0957-4166(03)00445-2

Reference yield:

2-methyl-4-oxo-cyclopent-2-enecarboxylic acid ethyl ester (17790-74-8) → (+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (613669-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ZnCl₂ / diethyl ether / 1 h / 20 °C

1.2: 91 percent / Ni(acac)2 / diethyl ether; tetrahydrofuran / 15 h / 20 °C

2.1: 93 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 3 h / -90 °C

3.1: Candida antartica B lipase / 7 h / 20 °C / Enzymatic reaction

4.1: 91 percent / Na₂CO₃ / methanol / 12 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; Candida antartica B lipase; sodium carbonate; zinc(II) chloride; In methanol; diethyl ether; ethanol; 2.1: Luche reduction;

DOI:10.1016/S0957-4166(03)00445-2

upstream raw materials:

vinyl acetate

(1S,2S,4R)-4-Acetoxy-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

2-methyl-4-oxo-cyclopent-2-enecarboxylic acid ethyl ester

para-methylphenylmagnesium bromide

Downstream raw materials:

(1S,2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

(1R,2R)-(1,2-dimethyl-2-p-tolyl-cyclopentyl)methanol