On May 24, 2004, Pallavicini, Marco; Bolchi, Cristiano; Di Pumpo, Raffaella; Fumagalli, Laura; Moroni, Barbara; Valoti, Ermanno; Demartin, Francesco published an article.Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one The title of the article was Resolution of 5-hydroxymethyl-2-oxazolidinone by preferential crystallization and investigations on the nature of the racemates of some 2-oxazolidinone derivatives. And the article contained the following:
After ascertaining its conglomerate nature by DSC and solid-state IR analyses, 5-hydroxymethyl-2-oxazolidinone (I), whose enantiomers are very important synthons, was efficiently resolved without chiral auxiliaries by preferential crystallization from a supersaturated isopropanolic solution of (±)-I, slightly enriched in one enantiomer (3.7% ee). Favorable conditions to the entrainment were defined utilizing a previously constructed ternary phase diagram of (R)-I, (S)-I, and 2-propanol. Furthermore, the investigations were extended to other chiral 2-oxazolidinones with a functionalized Me at the 5- or 4-position finding that 5-[(tosyloxy)methyl]-2-oxazolidinone is a racemic compound, whereas just the corresponding mesylate is a conglomerate as the parent alc. I. Interestingly, 4-(hydroxymethyl)-2-oxazolidinone proved to be a racemic compound in contrast with its positional isomer I demonstrating how a relatively fine variation in the mol. structure can unpredictably influence the crystalline nature of the racemate. The X-ray structure determination carried out on (S)-(+)-I, (±)-4-(hydroxymethyl)-2-oxazolidinone and (R)-(+)-4-(hydroxymethyl)-2-oxazolidinone enlightened the importance of the hydrogen bond in determining different supramol. assembling in the two homochiral compounds with respect to the racemic one and allowed a correlation with the stability of the crystal to be made. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one
The Article related to hydroxymethyl oxazolidinone resolution preferential crystallization, phase diagram hydroxymethyl oxazolidinone resolution preferential crystallization, differential scanning calorimetry hydroxymethyl oxazolidinone resolution preferential crystallization and other aspects.Reference of (R)-5-(Hydroxymethyl)oxazolidin-2-one
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem