(2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester

Base Information

• Chemical Name: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester
• CAS No.: 220993-22-6
• Molecular Formula: C₁₆H₃₁NO₄Si
• Molecular Weight: 329.512
• Mol file: 220993-22-6.mol

Synonyms:(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate

Chemical Property of (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester

Chemical Property:

Purity/Quality:

95-99% ^*data from raw suppliers

(2S)-2-[[tert-Butyldimethylsilyloxy]methyl]-4-oxo-1-pyrrolidinecarboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is used in the preparation of antibacterial oxazolidinone derivatives.

Technology Process of (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester

There total 9 articles about (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl 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: 95.0%

(2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (125653-58-9) → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate (220993-22-6)

Guidance literature:

(2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 - 0 ℃; for 1h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere;

Reference yield: 85.0%

→ (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate (220993-22-6)

Guidance literature:

Reference yield:

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0) → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate (220993-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / TEA; DMAP / CH₂Cl₂

2: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; TEA; trichloroisocyanuric acid; In dichloromethane;

DOI:10.1021/jo034214l

upstream raw materials:

(2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

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

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Downstream raw materials:

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylenepyrrolidine

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine

(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(4'-ethoxyphenyl)methylenepyrrolidine