(S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Base Information

• Chemical Name: (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one
• CAS No.: 845965-28-8
• Molecular Formula: C₂₂H₁₃F₁₂NO₂
• Molecular Weight: 551.332
• Mol file: 845965-28-8.mol

Synonyms:(S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Chemical Property of (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

There total 3 articles about (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-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: 61.0%

3,5-bis(trifluoromethyl)phenylmagnesium bromide (112981-69-8) + (S)-proline-N-ethyl carbamate methyl ester (77581-28-3,93423-88-2) → (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (845965-28-8)

Guidance literature:

In tetrahydrofuran; for 24h; Reflux;

DOI:10.1002/anie.201612048

Reference yield: 50.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) + (S)-proline-N-ethyl carbamate methyl ester (77581-28-3,93423-88-2) → (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (845965-28-8)

Guidance literature:

3,6-bis(trifluoromethyl)bromobenzene; With magnesium; In tetrahydrofuran; for 1h; Heating / reflux;

(S)-proline-N-ethyl carbamate methyl ester; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Heating / reflux;

With ammonium chloride; In tetrahydrofuran; water; at 20 ℃;

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1,1-bis(3,5-bis(trifluoromethyl)phenyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one (845965-28-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / K₂CO₃ / 0 - 20 °C

2: 58 percent / tetrahydrofuran / 0 - 65 °C

With potassium carbonate; In tetrahydrofuran;

DOI:10.1021/jo048378t

upstream raw materials:

3,5-bis(trifluoromethyl)phenylmagnesium bromide

(S)-proline-N-ethyl carbamate methyl ester

L-proline

3,6-bis(trifluoromethyl)bromobenzene

Downstream raw materials:

(S)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol