Selective N-debenzylation of benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses

Organic Letters

Volumn 2, Issue 12, 2000, Pages 1681-1683

  Kroutil, Jiri ^a   Trnka, Tomas ^a   Cerny, Miloslav ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

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Indexed keywords

EID: 0013326229     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005746g     Document Type: Article

References (19)

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17. Typical experimental procedure for N-debenzylation with DIAD: Method A (in toluene). To a solution of benzylamine 1 (1 mmol, 340 mg) in toluene (5 mL) was added DIAD (220 μL, 1.1 equiv), and the mixture was stirred at the given temperature until TLC showed no starting material. The mixture was concentrated in vacuo, and the resulting oil was treated with 5% NaOH in water-ethanol (in order to hydrolyze the DIHD) for several days at room temperature. After evaporation of ethanol and dilution with an equal volume of water, the debenzylated amine 2 was extracted with dichloromethane (repeatedly) and crystallized from a mixture of ethanol-ether-light petroleum ether. Method B (in pyridine-concentrated HCl mixture). A solution of benzylamine 1 (1 mmol, 340 mg), concentrated HCl (ca. 35%, 0.1 mL), and DIAD (220 μL, 1.1 equiv) in pyridine (5 mL) was heated to the given temperature until benzylamine disappeared. After evaporation of the solvent, the reaction mixture was treated following the same procedure as in method A.
18. Kroutil, J.; Trnka, T.; Budesinsky, M.; Cerny M. Collect. Czech. Chem. Commun. 1998, 63, 813.
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