(5S)-5-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-2-one

Base Information

• Chemical Name: (5S)-5-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-2-one
• CAS No.: 648424-62-8
• Molecular Formula: C12H25NO2Si
• Molecular Weight: 243.421
• DSSTox Substance ID: DTXSID90583296
• Nikkaji Number: J1.991.970F
• Wikidata: Q82474839
• Mol file: 648424-62-8.mol

Synonyms:648424-62-8;(5S)-5-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-2-one;DTXSID90583296

Chemical Property of (5S)-5-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-2-one

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 243.165455575
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCC1CCC(=O)N1
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OCC[C@@H]1CCC(=O)N1

Technology Process of (5S)-5-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)pyrrolidin-2-one

There total 1 articles about (5S)-5-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)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:

(S)-Pyroglutaminol (17342-08-4) → (S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)pyrrolidin-2-one (648424-62-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / Et₃N / CH₂Cl₂

2: 95 percent / dimethylsulfoxide

3: 55 percent / H₂SO₄; H₂O

4: 90 percent / NaBH₄ / methanol

5: 95 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium tetrahydroborate; sulfuric acid; water; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2007.02.008

Reference yield: 91.0%

4-bromobenzenecarbonitrile (623-00-7) + (S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)pyrrolidin-2-one (648424-62-8) → 4-[(2S)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-oxo-1-pyrrolidinyl]benzonitrile

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105 ℃; for 6h;

DOI:10.1016/j.tet.2003.11.008

Reference yield: 61.0%

methyl 2-bromo-5-nitrobenzoate (6942-36-5) + (S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)pyrrolidin-2-one (648424-62-8) → methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate (936114-10-2)

Guidance literature:

With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane;

DOI:10.1016/j.tetlet.2007.02.008

upstream raw materials:

(S)-Pyroglutaminol

Downstream raw materials:

methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate

(5S)-5-ethenyl-1-[4-iodo-2-formylphenyl]-2-pyrrolidinol

(5S)-5-ethenyl-1-[4-iodo-2-(hydroxymethyl)phenyl]-2-pyrrolidinone

methyl 5-iodo-2-[(5S)-5-(ethenyl)-2-oxo-1-pyrrolidinyl]benzoate