175659-77-5

Basic information

• Product Name: (αR)-N-[2-hydroxy-1-phenylethyl]-1,4-dihydro-2H-isoquinolin-3-one
• Synonyms: (αR)-N-[2-hydroxy-1-phenylethyl]-1,4-dihydro-2H-isoquinolin-3-one
• CAS NO: 175659-77-5
• Molecular Weight: 267.327
• Mol File: 175659-77-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (αR)-N-[2-hydroxy-1-phenylethyl]-1,4-dihydro-2H-isoquinolin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (αR)-N-[2-hydroxy-1-phenylethyl]-1,4-dihydro-2H-isoquinolin-3-one(175659-77-5)
• EPA Substance Registry System: (αR)-N-[2-hydroxy-1-phenylethyl]-1,4-dihydro-2H-isoquinolin-3-one(175659-77-5)

Safety Data

• Hazardous Substances Data: 175659-77-5(Hazardous Substances Data)

Upstream product

• 644-36-0 o-methylphenylacetic acid 
• 56613-80-0 D-2-phenylglycinol 
• 4385-35-7 isochroman-3-one 
• 39191-76-9 ethyl 2-(2-(bromomethyl)phenyl)acetate 
• 175659-83-3 2-[((R)-2-Hydroxy-1-phenyl-ethylamino)-methyl]-benzoic acid ethyl ester 

Downstream Products

• 175659-81-1 (4S*)-N-[(R)-2-hydroxy-1-phenylethyl]-4-benzyl-1,4-dihydroisoquinolin-3-one 
• 175777-31-8 (αR,4S)-N-[2-hydroxy-1-phenylethyl]-4-methyl-1,4-dihydro-2H-isoquinolin-3-one 

Relevant articles and documents

Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol. A novel asymmetric route to 4-phenyl-1,2,3,4-tetrahydroisoquinolines

(equation presented) Highly diastereoselective protonation of chiral lactam enolates of 4-substituted-1,4-dihydroisoquinolin-3-ones is reported. Protonation and alkylation processes of these lactam enolates derived from phenylglycinol occur with opposite diastereofacial selectivity. This diastereoselective protonation has been applied to the asymmetric synthesis of (4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 9 obtained in up to 97% ee.

Diastereoselective alkylation of homochiral 1,2,3,4-tetrahydroisoquinolin-3-one. A potential route to enantiomerically pure 4-substituted tetrahydroisoquinolines

Enantiomerically pure 1,4-dihydroisoquinolin-3-one 1 was prepared in four steps with an overall yield of 60%. Alkylation of the corresponding lactam enolate has been studied and has proven to be highly diastereoselective. Thus, 4-substituted-1,4-dihydroisoquinolin-3-ones 7a-d were obtained in high chemical yields with up to 97% diastereoisomeric excesses.