(1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester
• CAS No.: 113139-59-6
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.251
• Mol file: 113139-59-6.mol

Synonyms:

Chemical Property of (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester

There total 6 articles about (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl 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:

(1R,2S)-2-hydroxycyclohexanecarboxylic acid (1655-00-1) → (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester (113139-59-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridinium tosylate, 4 Angstroem molecular sieve / benzene

2: 1) LDA, PhSeCl, 2) H₂O₂ / 1) THF, from -70 deg C to 20 deg C, 2) CH₂Cl₂, pyridine

3: 75 percent / diethyl ether / 0 °C

4: 1) BuLi, 2) DMPU / 1) -70 deg C, THF

5: 1) Dowex 50 Wx₈ / 1) ethanol, 15 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; Phenylselenyl chloride; 4 A molecular sieve; DOWEX 50 WX₈; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium diisopropyl amide; In diethyl ether; benzene;

DOI:10.1016/S0040-4039(00)96385-8

Reference yield:

ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate (61586-78-5) → (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester (113139-59-6)

Guidance literature:

Multi-step reaction with 6 steps

1: LiOH / tetrahydrofuran; methanol; H₂O

2: 90 percent / pyridinium tosylate, 4 Angstroem molecular sieve / benzene

3: 1) LDA, PhSeCl, 2) H₂O₂ / 1) THF, from -70 deg C to 20 deg C, 2) CH₂Cl₂, pyridine

4: 75 percent / diethyl ether / 0 °C

5: 1) BuLi, 2) DMPU / 1) -70 deg C, THF

6: 1) Dowex 50 Wx₈ / 1) ethanol, 15 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; n-butyllithium; Phenylselenyl chloride; 4 A molecular sieve; DOWEX 50 WX₈; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water; benzene;

DOI:10.1016/S0040-4039(00)96385-8

Reference yield:

(2S,8aS)-2-(tert-butyl)-6,7,8,8a-tetrahydro-2H,4H-<1,3>benzodioxin-4-one (113121-90-7) → (1R,2S,6S)-2-Hydroxy-1,6-dimethyl-cyclohexanecarboxylic acid methyl ester (113139-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / diethyl ether / 0 °C

2: 1) BuLi, 2) DMPU / 1) -70 deg C, THF

3: 1) Dowex 50 Wx₈ / 1) ethanol, 15 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; DOWEX 50 WX₈; In diethyl ether;

DOI:10.1016/S0040-4039(00)96385-8

upstream raw materials:

diazomethane

(2S,4aR,5S,8aS)-2-tert-Butyl-4a,5-dimethyl-hexahydro-benzo[1,3]dioxin-4-one

(1R,2S)-2-hydroxycyclohexanecarboxylic acid

ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate