(R)-4-Benzyl-5,5-dimethyloxazolidin-2-one

Base Information

• Chemical Name: (R)-4-Benzyl-5,5-dimethyloxazolidin-2-one
• CAS No.: 204851-73-0
• Molecular Formula: C12H15 N O2
• Molecular Weight: 205.257
• European Community (EC) Number: 630-678-9
• DSSTox Substance ID: DTXSID70459425
• Nikkaji Number: J1.578.423G
• Wikidata: Q82283191
• Mol file: 204851-73-0.mol

Synonyms:(R)-4-Benzyl-5,5-dimethyloxazolidin-2-one;204851-73-0;(R)-(+)-4-Benzyl-5,5-dimethyl-2-oxazolidinone;(4R)-4-Benzyl-5,5-dimethyl-1,3-oxazolidin-2-one;SCHEMBL2369273;DTXSID70459425;AKOS015888877;BS-50396;CS-0098462;(4R)-4-Benzyl-5,5-dimethyloxazolidine-2-one;E78321;J-013349;(R)-(+)-4-Benzyl-5,5-dimethyl-2-oxazolidinone, 98%

Chemical Property of (R)-4-Benzyl-5,5-dimethyloxazolidin-2-one

Chemical Property:

• Vapor Pressure: 3.92E-06mmHg at 25°C
• Melting Point: 60-62 °C(lit.)
• Refractive Index: 1.519
• Boiling Point: 385°Cat760mmHg
• PKA: 12.86±0.60(Predicted)
• Flash Point: 186.7°C
• PSA: 38.33000
• Density: 1.085g/cm³
• LogP: 2.44490
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 205.110278721
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

NLT 98% ^*data from raw suppliers

(R)-(+)-4-Benzyl-5,5-dimethyl-2-oxazolidinone 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(NC(=O)O1)CC2=CC=CC=C2)C
• Isomeric SMILES: CC1([C@H](NC(=O)O1)CC2=CC=CC=C2)C
• Uses: Versatile chiral auxiliary for asymmetric synthesis used in diastereoselective Michael additions.

Technology Process of (R)-4-Benzyl-5,5-dimethyloxazolidin-2-one

There total 2 articles about (R)-4-Benzyl-5,5-dimethyloxazolidin-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: 55.0%

(R)-4-benzyl-3-[(2R,3S)-3-((1R,2R)-2-hexyl-cyclopropyl)-3-hydroxy-2-methyl-propionyl]-5,5-dimethyl-oxazolidin-2-one (1190324-42-5) → (R,R)-2-hexylcyclopropanecarboxaldehyde (441313-03-7) + (R)-4-benzyl-5,5-dimethyl-3-propionyloxazolidin-2-one (1190324-34-5) + (R)-(+)-4-benzyl-5,5-dimethyl-2-oxazolidinone (204851-73-0,352438-06-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -10 ℃; Inert atmosphere;

DOI:10.1039/b908600e

Reference yield:

(R)-2-Benzyl-3-hydroxy-3-methyl-butyric acid (204851-63-8) → (S)-4-benzyl-5,5-dimethyloxazolidin-2-one (168297-85-6,352438-06-3) + (R)-(+)-4-benzyl-5,5-dimethyl-2-oxazolidinone (204851-73-0,352438-06-3)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In toluene; at 80 ℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo9720804

Reference yield: 94.0%

isobutyryl chloride (79-30-1) + (R)-(+)-4-benzyl-5,5-dimethyl-2-oxazolidinone (204851-73-0,352438-06-3) → (R)-4-benzyl-3-isobutyryl-5,5-dimethyloxazolidin-2-one (1192188-15-0)

Guidance literature:

(R)-(+)-4-benzyl-5,5-dimethyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

isobutyryl chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.03.126

upstream raw materials:

(R)-2-Benzyl-3-hydroxy-3-methyl-butyric acid

(R)-4-benzyl-3-[(2R,3S)-3-((1R,2R)-2-hexyl-cyclopropyl)-3-hydroxy-2-methyl-propionyl]-5,5-dimethyl-oxazolidin-2-one

Downstream raw materials:

(R)-4-benzyl-3-(2-chloroacetyl)-5,5-dimethyl-2-one

(R)-3-(3-methylbutanoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one

(R)-4-benzyl-3-isobutyryl-5,5-dimethyloxazolidin-2-one

(R)-4-benzyl-3-(3-hydroxy-2,2-dimethylhexanoyl)-5,5-dimethyloxazolidin-2-one