(+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione

Base Information

• Chemical Name: (+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione
• CAS No.: 1428771-58-7
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 1428771-58-7.mol

Synonyms:(+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione

Chemical Property of (+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione

There total 2 articles about (+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione 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: 50.0%

C30H30NO5P (1428771-50-9) + benzaldehyde (100-52-7) → (+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione (1428771-58-7)

Guidance literature:

C₃₀H₃₀NO₅P; With potassium tert-butylate; In tetrahydrofuran; for 0.333333h; Inert atmosphere; Reflux;

benzaldehyde; In tetrahydrofuran; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2013.03.004

Reference yield:

5(S)-N-tert-butoxycarbonyl-4-hydroxy-5-methyl-3-pyrrolin-2-one (223678-66-8) → (+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione (1428771-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 16.33 h / Reflux; Heating

2.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / Inert atmosphere; Reflux

2.2: 12 h / Inert atmosphere; Reflux

With potassium tert-butylate; In tetrahydrofuran; 2.2: |Wittig Olefination;

DOI:10.1016/j.tet.2013.03.004

Reference yield: 25.0%

(+)-(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-hydroxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione (1428771-58-7) + trimethoxonium tetrafluoroborate (420-37-1) → (5S)-N-tert-butoxycarbonyl-3-[(E)-1'-methoxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione (1428771-59-8)

Guidance literature:

With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at 70 ℃; for 1h; regioselective reaction; Microwave irradiation;

DOI:10.1016/j.tet.2013.03.004

upstream raw materials:

C₃₀H₃₀NO₅P

benzaldehyde

5(S)-N-tert-butoxycarbonyl-4-hydroxy-5-methyl-3-pyrrolin-2-one

Downstream raw materials:

(5S)-N-tert-butoxycarbonyl-3-[(E)-1'-methoxy-3'-phenylallylidene]-5-methylpyrrolidine-2,4-dione