1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 1026986-39-9
• Molecular Formula: C₂₁H₃₃NO₃
• Molecular Weight: 347.498
• Mol file: 1026986-39-9.mol

Synonyms:1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of 1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of 1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester

There total 1 articles about 1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic 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:

2,4-di-tertbutyl-6-chloromethylphenol (10193-84-7) + L-proline methyl ester monohydrochloride (2133-40-6) → 1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester (1026986-39-9)

Guidance literature:

L-proline methyl ester monohydrochloride; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

2,4-di-tertbutyl-6-chloromethylphenol; With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1002/ejoc.200300415

Reference yield: 70.0%

phenylmagnesium bromide + 1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester (1026986-39-9) → (S)-1-[3',5'-di-(tert-butylphenyl)methyl]-2-(hydroxydiphenylmethyl)pyrrolidine

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200300415

Reference yield:

1-(3,5-di-tert-butyl-2-hydroxy-benzyl)-pyrrolidine-2-carboxylic acid methyl ester (1026986-39-9) → (1R,2S)-1-[(3',5'-di-tert-butylphenyl)methyl]-2-(hydroxydiphenylmethyl)pyrrolidine N-oxide

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / tetrahydrofuran / 24 h / 20 °C

2: 99 percent / m-perchlorobenzoic acid; K₂CO₃ / CH₂Cl₂ / -78 - 20 °C

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1: Grignard reaction;

DOI:10.1002/ejoc.200300415

upstream raw materials:

2,4-di-tertbutyl-6-chloromethylphenol

L-proline methyl ester monohydrochloride