3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide

Base Information

• Chemical Name: 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide
• CAS No.: 1198800-73-5
• Molecular Formula: Br*C₂₆H₃₂N₃O₃
• Molecular Weight: 514.462

Synonyms:3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide

Chemical Property of 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide

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Technology Process of 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide

There total 8 articles about 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide 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: 94.0%

3-(5-((3R,5S)-1-benzyl-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide (1198800-72-4) → 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide (1198800-73-5)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃;

DOI:10.1002/ejoc.200900807

Reference yield: 85.0%

3-(5-(((3R,5S)-1-(tert-butoxycarbonyl)-5-(hydroxydiphenylmethyl) pyrrolidin-3-yl) oxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide → 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide (1198800-73-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h;

DOI:10.1016/j.molcata.2014.12.009

Reference yield:

5-bromopentanoic acid (2067-33-6) → 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide (1198800-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 1.5 h / 0 °C / Reflux

2: diethyl ether / 0.17 h / 100 °C

3: trifluoroacetic acid / dichloromethane / 2 h

With dmap; dicyclohexyl-carbodiimide; trifluoroacetic acid; In diethyl ether; dichloromethane;

DOI:10.1016/j.molcata.2014.12.009

upstream raw materials:

3-(5-((3R,5S)-1-benzyl-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide

5-bromopentanoic acid

(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester

4R-4-hydroxyproline

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