152547-73-4

Upstream product

• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 74-88-4 methyl iodide 
• 13626-76-1 3-methyl-4-phenyloxazol-2(3H)-one 
• 84773-28-4 (R)-2-(methylamino)-2-phenylethanol 
• 152547-72-3 (R)-tert-butyl N-(2-hydroxy-1-phenylethyl)-N-methylcarbamate 

Downstream Products

• 158805-39-1 (4R-cis) 3-[(10,11-dihydro-5H dibenzo[a,d]cyclohepten-5-yl)acetyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 1027345-63-6 N-[(R)-2-hydroxy-1-phenylethyl]-N-methylheptanamide 
• 1027345-62-5 N-[(R)-2-hydroxy-1-phenylethyl]-N-methylpropionamide 
• 160247-37-0 N-[(R)-2-hydroxy-1-phenylethyl]-N-methyl-2-phenylacetamide 
• 1027345-61-4 N-[(R)-2-hydroxy-1-phenylethyl]-N-methylbut-3-enamide 
• 147900-34-3 (4R-cis)-3-[(5H-Dibenzo[a,d]cyclohepten-5-yl)acetyl]-4-methyl-5-phenyl-2-oxazolidinone 

Relevant academic research and scientific papers

Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)-NHC-catalysed asymmetric hydrogenation of 2-oxazolones

An efficient synthesis of optically active 4-substituted 2-oxazolidinones by the ruthenium(ii)-NHC-catalysed asymmetric hydrogenation of 2-oxazolones was developed. Excellent enantioselectivities (up to 96% ee) and yields (up to 99%) were obtained for a variety of substrates, bearing a range of functional groups and useful motifs. The hydrogenation reaction was successfully scaled up to gram scale using low catalyst loading. Moreover, the utility of this methodology was demonstrated by the transformation of the enantioenriched product into the corresponding chiral β-amino alcohol, a bisoxazoline ligand, and the formal synthesis of (-)-aurantioclavine.

Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents

Treatment of N-alkyl-oxazolidin-2-ones with Grignard reagents gives tertiary carboxylic amide products. Various substituted oxazolidinones can be used as illustrated with phenyl, benzyl or isopropyl groups on the 4-position, and methyl, benzyl or p-methox

Heterocyclizations of N-Boc derivatives of β-amino alcohols and thio analogs: an unusual case of the Thorpe-Ingold effect

Enantiopure oxazolidin-2-ones were synthesized from chiral N-Boc β-aminoalcohols which underwent a cyclization upon treatment with tosyl chloride.This reaction was strongly accelerated in the case of carbamates derived from N-methylated amines.A similar heterocyclization was observed with dithiocarbamates, ie sulfur analogs of carbamates.The rate enhancement due to the nitrogen substitution was studied by AM1 calculations. - Keywords: carbamate; dithiocarbamate; oxazolidinone; thiazolidinone; AM1 calculations

Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity

Treatment of N-tert-butoxycarbonyl derivatives of homochiral β-amino alcohols with p-toluenesulfonyl chloride affords 2-axazolidinones. These heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect was studied by AMI calculations.