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

Base Information

• Chemical Name: methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate
• CAS No.: 936114-10-2
• Molecular Formula: C₂₀H₃₀N₂O₆Si
• Molecular Weight: 422.553
• Mol file: 936114-10-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate 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: 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

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate (936114-10-2)

Guidance literature:

Multi-step reaction with 6 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

6: 61 percent / xantphos; Cs₂CO₃ / Pd₂dba3 / dioxane

With 1H-imidazole; sodium tetrahydroborate; sulfuric acid; water; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2007.02.008

Reference yield:

methyl (S)-2-(5-oxopyrrolidin-2-yl)acetate (67036-44-6) → methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate (936114-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaBH₄ / methanol

2: 95 percent / imidazole / dimethylformamide

3: 61 percent / xantphos; Cs₂CO₃ / Pd₂dba3 / dioxane

With 1H-imidazole; sodium tetrahydroborate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2007.02.008

upstream raw materials:

methyl 2-bromo-5-nitrobenzoate

(S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)pyrrolidin-2-one

2-[(2S)-5-oxopyrrolidin-2-yl]acetonitrile

(S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester

Downstream raw materials:

(3aS,4S,9bS)-8-iodo-2,3,3a,4,5,9b-hexahydro-1-(phenylmethyl)-1H-pyrrolo[3,2-c]quinoline-4-propanol

(3aS,4S,9bS)-8-iodo-2,3,3a,4,5,9b-hexahydro-5-(3-oxobutanoyl)-1-(phenylmethyl)-1H-pyrrolo-[3,2-c]quinoline-4-propyl acetate

methyl (3aS,4S,9bS)-2,3,3a,4,5,9b-hexahydro-5-(3-oxobutanoyl)-1-(phenylmethyl)-1H-pyrrolo-[3,2-c]quinoline-8-carboxylate

methyl (3aS,4S,9bS)-2,3,3a,4,5,9b-hexahydro-5-(3-oxobutanoyl)-1-(phenylmethyl)-5-(trifluoroacetyl)-1H-pyrrolo[3,2-c]quinoline-8-carboxylate