152903-44-1

Basic information

• Product Name: (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
• Synonyms: (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
• CAS NO: 152903-44-1
• Molecular Weight: 281.311
• Mol File: 152903-44-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione(152903-44-1)
• EPA Substance Registry System: (+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione(152903-44-1)

Safety Data

• Hazardous Substances Data: 152903-44-1(Hazardous Substances Data)

Upstream product

• 176538-77-5 2-((4S,5S)-2-Oxo-4-phenyl-2λ⁴-[1,3,2]dioxathian-5-yl)-isoindole-1,3-dione 
• 123537-84-8 (1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 85-44-9 phthalic anhydride 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 

Downstream Products

• 152903-48-5 (+)-N,N-Phthaloyl-O¹-tosyl-D-phenylalaninol 
• 77210-49-2 R-(+)-2-amino-3-fluoro-1-phenylpropane 
• 321936-55-4 (+)-(R)-2-[1-benzyl-2-(2,6-dimethylphenoxy)ethyl]-1H-isoindole-1,3(2H)-dione 
• 321936-74-7 (-)-(R)-α-[(2,6-dimethylphenoxy)methyl]benzeneethanamine 
• 856421-78-8 S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate 
• 911067-68-0 2-((1R,2S)-1-Benzyl-2-hydroxy-3-nitro-propyl)-isoindole-1,3-dione 
• 870839-74-0 (R)-2-(1-fluoromethyl-2-phenylethyl)isoindol-1,3-dione 
• 166734-67-4 (R)-2-phthalimido-3-phenylpropionaldehyde 
• 467250-83-5 (1'R,3RS)-2-(2'-benzyl-1'-hydroxyethyl)-2,3-dihydro-3-hydroxy-1H-isoindol-1-one 
• 74397-35-6 (+)-(R)-2-(1-benzyl-2-iodoethyl)-1H-isoindole-1,3(2H)-dione 
• 162088-28-0 (+)-(R)-2-(1-benzyl-2-bromoethyl)-1H-isoindole-1,3(2H)-dione 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 74397-33-4 (2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate 

Relevant articles and documents

Synthesis of N-phthalimido β-aminoethanesulfonyl chlorides: The use of thionyl chloride for a simple and efficient synthesis of new peptidosulfonamide building blocks

N-Phthalimido β-aminoethanesulfonyl chlorides, new building blocks for the synthesis of peptidosulfonamide peptidomimetics, were prepared in a straightforward manner from amino acids. In the crucial synthetic step, sulfonic acids or their sodium salts were converted into the corresponding sulfonyl chlorides using an excess of refluxing thionyl chloride or thionyl chloride/DMF. This simple and effective chlorinating method is also applicable to β-aminoethane sulfonic acids and their sodium salts with other N-protecting groups.

Diastereoselective access to chiral non-racemic [1,3]oxazolo-[2,3-a] isoindol-5-one ring systems via o-cationic cyclization

The title compounds 4 have been prepared from suitable β-amino-alcohol 2 and phthalic anhydride (5) in a three-step sequence in moderate to good yields (58-94%). The key step of this methodology is based on an intramolecular O-cationic cyclization involving N-acyliminium species. The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.

(1S,2S)-2-Amino-1-phenyl-1,3-propanediol, a spin off from chloramphenicol manufacture, as chiral synthon for (1S, 2S)-pseudoephedrine and (R)-phenylalaninol

(1S,2S)-2-Amino-1-phenyl-1,3-propanediol (3a), a discarded optically active material in one of the processes for the manufacture of chloramphenicol, has been transformed into (S,S)-pseudoephedrine (4) and (R)-phenylalaninol (5). The opposite selectivity of highly regioselective oxidative ring opening of the benzaldehyde acetal of (1S,2S)-2-phthalimido-1-phenyl-1,3-propanediol by NBS and highly regioselective ring opening of the cyclic sulphite of the same substrate by LiBr are the key steps in the transformations respectively.