87554-50-5Relevant articles and documents
Heterocyclic GABA Agonists. Synthesis and Crystal Structure of (RS)-5-(N-t-Butyloxycarbonylaminomethyl)-3-oxoisoxazolidine-2-carboxamide, a Derivative of Dihydromuscimol
Brehm, Lotte,Jacobsen, Poul,Johansen Joergen S.,Krogsgaard-Larsen, Povl
, p. 1459 - 1464 (2007/10/02)
Reaction of the O- and N-protected (RS)-3-hydroxy-4-aminobutyric acid ester (4) with hydroxyurea under basic conditions unexpectedly yielded (RS)-5-(N-t-butyloxycarbonylaminomethyl)-3-oxoisoxazolidine-2-carboxamide (8), the structure of which has been confirmed by an X-ray analysis.Elimination of the cyanate ion, which could be trapped with dimethylamine, converted (8) into the corresponding 2-isoxazolin-3-ol derivative (7).Attempts to prepare the individual enantiomers of (8) were unsuccessful.The (R)-(-)-3-hydroxy-4-aminobutyric acid derivative (5) yielded racemic (8).The cyclization reaction of (5) and (4) are believed to involve elimination of toluene-4-sulphonate giving the corresponding α,β-unsaturated ester as an intermediate.