1240815-99-9

Basic information

• Product Name: N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone
• Synonyms: N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone
• CAS NO: 1240815-99-9
• Molecular Weight: 321.351
• Mol File: 1240815-99-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone(1240815-99-9)
• EPA Substance Registry System: N-(4-fluorophenyl)-α-(4-benzyloxyphenyl)nitrone(1240815-99-9)

Safety Data

• Hazardous Substances Data: 1240815-99-9(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 350-46-9 4-Fluoronitrobenzene 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 406-00-8 4-fluoro-N-hydroxyaniline 
• 415960-63-3 N-(4-(benzyloxy)benzyl)-4-fluoroaniline 
• 1206694-75-8 4-(2-aza-2-(4-fluorophenyl)vinyl)-1-benzyloxybenzene 

Downstream Products

• 1240816-36-7 (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-(4-fluorophenyl)azetidin-2-one 
• 1240816-39-0 (3R,4S)-4-(4-(benzyloxy)phenyl)-3-((1'R)-1',2'-dihydroxyethyl)-1-(4-fluorophenyl)-azetidin-2-one 
• 1240816-59-4 (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-formyl-azetidin-2-one 
• 221349-58-2 (2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde 
• 1316784-95-8 C₂₇H₂₆FNO₄ 
• 1316784-92-5 C₂₇H₂₆FNO₄ 
• 1316784-90-3 C₂₇H₂₆FNO₄ 
• 163222-33-1 ezetemibe 
• 1416263-38-1 (6S)-3-((R)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)-methyl)-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one 
• 1445455-42-4 C₃₁H₂₇F₂NO₄ 
• 1416263-37-0 (3S,3aS,6S,7aS)-3-(4-(benzyloxy)phenyl)-2,6-bis(4-fluorophenyl)tetrahydro-2H-pyrano[3,4-d]isoxazol-4(6H)-one 
• 1445455-31-1 (3S,6R)-3-(S)-(4-benzyloxyphenyl)-(4-fluorophenyl)aminomethyl-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one 
• 163380-15-2 (3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one 
• 163222-32-0 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone 

Relevant articles and documents

Total synthesis of ezetimibe, a cholesterol absorption inhibitor

Ezetimibe (1), a strong β-lactamic cholesterol absorption inhibitor, was synthesized from (R)-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one 7. Independent pathways were analyzed in order to select the optimal one, which involved 1,3-dipolar cycloaddition with C-(4-benzyloxyphenyl)-N-(4-fluorophenyl) -nitrone (8), intramolecular nucleophilic displacement at the benzylic position of the lactone, cleavage of the N-O bond, elimination of a water molecule, hydrogenation of the double bond, rearrangement of the six-membered lactone ring into a β-lactam moiety, and final deprotection of the phenolic hydroxyl group. Highly stereoselective Sc(OTf)3-catalyzed 1,3-dipolar cycloaddition was the most crucial step of the synthesis. Owing to the rigid transition state of the cycloaddition, the absolute configuration of the starting lactone controlled the formation of other stereogenic centers of the final molecule 1.

A PROCESS FOR THE PREPARATION OF AN ALDEHYDE BETA-LACTAM COMPOUND

The invention relates to a process for the preparation of an aldehyde beta-lactam compound of formula (I), wherein P1 is H or a protecting group, useful in the preparation of ezetimibe, from a nitrone compound of formula (II). The nitrone compound Il is prepared by reacting 4-fluorophenylhydroxyloamine with OH- protected 4-hydroxybenzaldehyde. The nitrone compound of formula (II) is reacted with an acetylene compound of formula (III) to form a compound of formula (IV), and the compound of formula (IV), after optional deprotection, is oxidized to obtain an aldehyde of formula (V), which undergoes isomerisation to the compound of formula (I). The subject of the invention are also novel compounds of formulas (II) and (IV).