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  • Title: A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol.
    Author: Clinch K, Evans GB, Furneaux RH, Lenz DH, Mason JM, Mee SP, Tyler PC, Wilcox SJ.
    Journal: Org Biomol Chem; 2007 Sep 07; 5(17):2800-2. PubMed ID: 17700848.
    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.
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