(4R,8aS)-4-Phenyl-8a-(trifluoromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-one

Base Information

• Chemical Name: (4R,8aS)-4-Phenyl-8a-(trifluoromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-one
• CAS No.: 921224-81-9
• Molecular Formula: C14H14F3NO2
• Molecular Weight: 285.266
• DSSTox Substance ID: DTXSID90580442
• Nikkaji Number: J2.404.751B
• Wikidata: Q82471278
• Mol file: 921224-81-9.mol

Synonyms:921224-81-9;DTXSID90580442;(4R,8aS)-4-Phenyl-8a-(trifluoromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-one

Chemical Property of (4R,8aS)-4-Phenyl-8a-(trifluoromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-one

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 285.09766318
• Heavy Atom Count: 20
• Complexity: 392

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2(C(=O)OCC(N2C1)C3=CC=CC=C3)C(F)(F)F
• Isomeric SMILES: C1C[C@]2(C(=O)OC[C@H](N2C1)C3=CC=CC=C3)C(F)(F)F

Technology Process of (4R,8aS)-4-Phenyl-8a-(trifluoromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-one

There total 6 articles about (4R,8aS)-4-Phenyl-8a-(trifluoromethyl)hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-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: 25.0%

(4R)-7-iodo-4-phenyl-8a-trifluoromethylhexahydropyrrolo[2,1-c][1,4]oxazin-1-one → (4R,8aR)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one + (4R,8aS)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one (921224-81-9)

Guidance literature:

With palladium on carbon; hydrogen; sodium acetate; In ethanol; at 20 ℃; for 24h; under 3750.38 Torr;

DOI:10.1021/ol8024567

Reference yield:

1-(2-hydroxy-1-phenylethyl)-2-carbonitrile-2-trifluoromethylpyrrolidine → (4R,8aR)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one + (4R,8aS)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one (921224-81-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 110 ℃; for 24h; Dean-Stark;

DOI:10.1039/d1ob01173a

Reference yield:

(4R,8aS)-7-iodo-4-phenyl-8a-trifluoromethylhexahydropyrrolo[2,1-c][1,4]oxazin-1-one → (4R,8aR)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one + (4R,8aS)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one (921224-81-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; sodium acetate; In ethanol; for 24h; under 3750.38 Torr;

DOI:10.1016/j.ejmech.2012.12.041

upstream raw materials:

ethyl-3,3,3-trifluoropyruvate

D-2-phenylglycinol

allyl-trimethyl-silane

(4R)-2-ethoxycarbonyl-2-trifluoromethyl-4-phenyl-1,3-oxazolidine

Downstream raw materials:

(S)-α-trifluoromethyl-prolinol

(S)-α-trifluoromethyl-proline