(R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

Base Information

• Chemical Name: (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester
• CAS No.: 143347-67-5
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.255
• Mol file: 143347-67-5.mol

Synonyms:(R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

Chemical Property of (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

There total 1 articles about (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl 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: 85.0%

(S)-N-methyl-2-hydroxysuccinimide acrylate (126983-29-7) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → (R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester (143347-67-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00045a013

Reference yield: 98.0%

(R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester (143347-67-5) → (R)-cyclohex-3-enecarboxylic acid (5709-98-8)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo00045a013

Reference yield:

(R)-Cyclohex-3-enecarboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester (143347-67-5) → tert-Butyl-((1R,2R,4R)-4-ethynyl-2-methoxy-cyclohexyloxy)-diphenyl-silane (143347-72-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / LiOH, H₂O₂ / tetrahydrofuran / 0 °C

2: 1) MCPBA, 2) Et₃N, SiO₂ / 1) CCl₄, 0 to 25 deg C, 2) 70 deg C

3: 90 percent / imidazole / dimethylformamide / 25 °C

4: NaHCO₃ / 25 °C

5: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 25 °C

6: 100 percent / LiAlH₄ / diethyl ether / 0 °C

7: 1) (COCl)2, DMSO, 2) NEt₃ / 2) CH₂Cl₂, -78 deg C

8: 83 percent / NaH / tetrahydrofuran / -78 °C

With 1H-imidazole; lithium hydroxide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; dihydrogen peroxide; silica gel; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00045a013

upstream raw materials:

(S)-N-methyl-2-hydroxysuccinimide acrylate

buta-1,3-diene

Downstream raw materials:

(R)-cyclohex-3-enecarboxylic acid

tert-Butyl-((1R,2R,4R)-4-ethynyl-2-methoxy-cyclohexyloxy)-diphenyl-silane

(1R,3R,4R)-4-[((1,1-dimethylethyl)diphenylsilyl)-oxy]-3-methoxy-cyclohexanemethanol

(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexanecarbaldehyde

Refernces