title: A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol.
abstract: The title compound (+)-, required for production of transition state analogue inhibitors of enzymes involved in T-cell-dependent disorders, was synthesized in five steps. A 1,3-dipolar cycloaddition of the nitrone formed from formaldehyde and N-benzylhydroxylamine to diethyl maleate gave the racemic cis-isoxazolidine (+/-)-. Reduction of the N-O bond of this compound gave pyrrolidone (+/-)- in excellent yield. A very efficient enzymic resolution of this racemic product led to the title enantiomer (+)-. This route employs only one chromatographic purification.
authors: Carbohydrate Chemistry Team, Industrial Research Ltd, P.O. Box 31310, Lower Hutt, New Zealand.
authors: Keith
authors: K
authors: Clinch
authors: Gary B
authors: GB
authors: Evans
authors: Richard H
authors: RH
authors: Furneaux
authors: Dirk H
authors: DH
authors: Lenz
authors: Jennifer M
authors: JM
authors: Mason
authors: Simon P H
authors: SP
authors: Mee
authors: Peter C
authors: PC
authors: Tyler
authors: Sarah J
authors: SJ
authors: Wilcox
mesh_terms: D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C524129:N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol; D011759:Pyrrolidines