(S)-3,3,6,6-TETRAMETHYLTETRAHYDROPYRROLO[1,2-C]OXAZOL-5(3H)-ONE

Base Information

• Chemical Name: (S)-3,3,6,6-TETRAMETHYLTETRAHYDROPYRROLO[1,2-C]OXAZOL-5(3H)-ONE
• CAS No.: 156088-45-8
• Molecular Formula: C₁₀H₁₇NO₂
• Molecular Weight: 183.25
• Hs Code.: 2934999090
• Mol file: 156088-45-8.mol

Synonyms:(5S)-1-aza-2,2-dimethyl-7,7-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane

Chemical Property of (S)-3,3,6,6-TETRAMETHYLTETRAHYDROPYRROLO[1,2-C]OXAZOL-5(3H)-ONE

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(S)-3,3,6,6-Tetramethyltetrahydropyrrolo[1,2-C]oxazol-5(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (S)-3,3,6,6-TETRAMETHYLTETRAHYDROPYRROLO[1,2-C]OXAZOL-5(3H)-ONE

There total 4 articles about (S)-3,3,6,6-TETRAMETHYLTETRAHYDROPYRROLO[1,2-C]OXAZOL-5(3H)-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: 86.0%

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (99208-71-6) + methyl iodide (74-88-4) → (5S)-1-aza-2,2-dimethyl-7,7-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (156088-45-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(02)00166-0

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (5S)-1-aza-2,2-dimethyl-7,7-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (156088-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / PTSA / toluene / 4 h / Heating

2: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C

With toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; toluene;

DOI:10.1016/S0957-4166(02)00166-0

Reference yield:

L-Pyroglutamic acid (98-79-3) → (5S)-1-aza-2,2-dimethyl-7,7-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane (156088-45-8)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄ / toluene / 6 h / Heating

2: 31.2 g / NaBH₄ / ethanol / 1.5 h / 0 - 20 °C

3: 95 percent / PTSA / toluene / 4 h / Heating

4: 86 percent / LDA / tetrahydrofuran / -78 - 20 °C

With sodium tetrahydroborate; sulfuric acid; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; ethanol; toluene;

DOI:10.1016/S0957-4166(02)00166-0

upstream raw materials:

(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane

methyl iodide

(S)-Pyroglutaminol

L-Pyroglutamic acid

Downstream raw materials:

(5S)-1-(2,2-dimethylpropionyl)-3,3-dimethyl-5-trityloxymethylpyrrolidin-2-one

(S)-3,3-Dimethyl-1-(3-phenyl-propionyl)-5-trityloxymethyl-pyrrolidin-2-one

(5S)-(-)-3,3-dimethyl-5-triphenylmethoxymethyl-1-propionyl-pyrrolidin-2-one

(5S)-(-)-5-tert-butyldimethylsiloxymethyl-3,3-dimethyl-1-(3-phenylpropionyl)-pyrrolidin-2-one

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