(3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one

Base Information

• Chemical Name: (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one
• CAS No.: 849624-40-4
• Molecular Formula: C₁₈H₂₈N₄O₄SSi
• Molecular Weight: 424.596
• Mol file: 849624-40-4.mol

Synonyms:(3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one

Chemical Property of (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one

There total 3 articles about (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one 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:

p-toluenesulfonyl chloride (98-59-9) + (3R,5S)-5-Azidomethyl-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one → (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one (849624-40-4)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.tetasy.2004.12.018

Reference yield:

(2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine (114676-68-5) → (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one (849624-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NaIO₄; RuO₂*xH₂O / ethyl acetate; H₂O / 10 h / 20 °C

2: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

3: 2.9 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 °C

With dmap; ruthenium(IV) oxide; sodium periodate; trifluoroacetic acid; In dichloromethane; water; ethyl acetate;

DOI:10.1016/j.tetasy.2004.12.018

Reference yield:

(3R,5S)-5-azidomethyl-1-(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]pyrrolidin-2-one (849624-32-4) → (3R,5S)-1-azidomethyl-3-(tert-butyldimethylsilyloxy)-1-(p-toluenesulfonyl)pyrrolidin-2-one (849624-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

2: 2.9 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 °C

With dmap; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tetasy.2004.12.018

upstream raw materials:

p-toluenesulfonyl chloride

(2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

(3R,5S)-5-azidomethyl-1-(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]pyrrolidin-2-one