(R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole

Base Information

• Chemical Name: (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole
• CAS No.: 21399-39-3
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.257
• Mol file: 21399-39-3.mol

Synonyms:

Chemical Property of (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole

There total 8 articles about (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole 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:

(R)-2-(4-Methoxy-benzyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (120349-79-3) → (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole (21399-39-3,22862-67-5,111687-94-6,120409-91-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 4h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)80511-0

Reference yield:

methyl (R)-2-amino-3-(4-methoxyphenyl)propanoate (17355-19-0,61780-18-5,120349-74-8) → (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole (21399-39-3,22862-67-5,111687-94-6,120409-91-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / Na₂CO₃ / dioxane; H₂O / Ambient temperature

2: 95 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / Ambient temperature

3: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 °C

4: 18-crown-6, (Me₃Si)2NK / tetrahydrofuran / -78 °C

5: 98 percent / DIBAH / CH₂Cl₂ / -78 °C

6: 93 percent / Et₃N / CH₂Cl₂ / 0.33 h / -10 °C

7: 94 percent / NaH / CH₂Cl₂ / Ambient temperature

8: CF₃CO₂H / CH₂Cl₂ / 4 h / Ambient temperature

With sodium tetrahydroborate; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)80511-0

Reference yield:

(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester (94790-24-6) → (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole (21399-39-3,22862-67-5,111687-94-6,120409-91-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / Ambient temperature

2: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 °C

3: 18-crown-6, (Me₃Si)2NK / tetrahydrofuran / -78 °C

4: 98 percent / DIBAH / CH₂Cl₂ / -78 °C

5: 93 percent / Et₃N / CH₂Cl₂ / 0.33 h / -10 °C

6: 94 percent / NaH / CH₂Cl₂ / Ambient temperature

7: CF₃CO₂H / CH₂Cl₂ / 4 h / Ambient temperature

With sodium tetrahydroborate; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)80511-0

upstream raw materials:

(R)-2-(4-Methoxy-benzyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

methyl (R)-2-amino-3-(4-methoxyphenyl)propanoate

(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester

[(R)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Refernces