(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate
• CAS No.: 1269755-81-8
• Molecular Formula: C₂₉H₄₃NO₅Si
• Molecular Weight: 513.75
• Mol file: 1269755-81-8.mol

Synonyms:(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

Chemical Property of (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

There total 4 articles about (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate 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:

(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (887923-73-1) + 2-Bromoethyl methyl ether (6482-24-2) → (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate (1269755-81-8)

Guidance literature:

(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate; With sodium hydride; In tetrahydrofuran; mineral oil; at 25 ℃; for 1h;

2-Bromoethyl methyl ether; In tetrahydrofuran; mineral oil; at 25 ℃; for 18h;

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate (1269755-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 18 h / 20 °C

2.1: sodium tetrahydroborate / tetrahydrofuran / 4 h / 70 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 25 °C

3.2: 18 h / 25 °C

With 1H-imidazole; sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; dichloromethane;

Reference yield:

(2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1157902-48-1) → (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate (1269755-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 4 h / 70 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 25 °C

2.2: 18 h / 25 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran;

upstream raw materials:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

2-Bromoethyl methyl ether

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2S,4S)-tert-butyl 4-hydroxy-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

(2S,4S)-tert-butyl 2-((2-methoxyethoxy)methyl)-4-(tosyloxy)pyrrolidine-1-carboxylate