1393737-41-1

Basic information

• Product Name: (4R,αS)-4-(3,4-dichlorobenzyl)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone
• Synonyms: (4R,αS)-4-(3,4-dichlorobenzyl)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone
• CAS NO: 1393737-41-1
• Molecular Weight: 380.271
• Mol File: 1393737-41-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4R,αS)-4-(3,4-dichlorobenzyl)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,αS)-4-(3,4-dichlorobenzyl)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone(1393737-41-1)
• EPA Substance Registry System: (4R,αS)-4-(3,4-dichlorobenzyl)-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone(1393737-41-1)

Safety Data

• Hazardous Substances Data: 1393737-41-1(Hazardous Substances Data)

Upstream product

• 1393737-34-2 diethyl (S)-2-(3,4-dichlorobenzyl)-2-((α-methylbenzyl)amino)malonate 
• 74124-79-1 di(succinimido) carbonate 
• 1393737-38-6 (S)-2-(3,4-dichlorobenzyl)-2-((α-methylbenzyl)amino)-1,3-propanediol 
• 627-11-2 2-Chloroethyl chloroformate 
• 1393737-32-0 diethyl (S)-2-(3,4-dichlorobenzyl)-2-((α-methylbenzyl)amino)malonate hydrochloride 
• 18880-04-1 3,4-dichlorobenzyl bromide 

Downstream Products

• 1393737-48-8 (R)-4-(3,4-dichlorobenzyl)-4-hydroxymethyl-2-oxazolidinone 
• 112922-55-1 (S)-3-(3,4-dichlorophenyl)-2-dimethylamino-2-methyl-1-propanol 

Relevant articles and documents

Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2- oxazolidinones: Asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377

A reaction of (S)-2-benzyl-2-(α-methylbenzyl)amino-1,3-propanediol (S)-4a and 2-chloroethyl chloroformate, and the subsequent addition of DBU gave (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (4R)-5a (92% de) via a diastereoselective asymmetric desymmetrization process. Debenzylation of (4R)-5a using trifluoromethanesulfonic acid and anisole in MeNO2 gave (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone (R)-15a, which was converted into (R)-(α-hydroxymethyl)phenylalanine (7) in two steps. N-Boc-α-methylphenylalanine (8), cericlami0ne (9) and BIRT-377 (10) were also synthesized using these asymmetric desymmetrization and debenzylation.