1-Bromonaphthalene-2-carbaldehyde → (1-Bromonaphthalen-2-yl)methanol
Reaktionsgleichung
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[O:13].[BH4-].[Na+]>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][OH:13]Komponenten
3
Versuchsvorschrift
Scheme 3 also shows a general synthetic route to compounds of formula I. Reaction of 1-bromo-2-naphthaldehyde with sodium borohydride provided 1-bromo-2-naphthalenemethanol (xiv). Alcohol (xiv) was reacted with BOC-protected sulfonamide (xc), triphenylphosphine and diethyl azodicarboxylate to provide sulfonamide (xv). The sulfonamide was reacted with tert-butyllithium at a temperature between about -90° C. and about 10° C. in THF to provide (xvi). The nitrogen of compound (xvi) was protected as the benzyl carbamate by treating (xvi) with sodium hydride and benzylchloroformate, and the tert-butyl ester was then hydrolyzed with trifluoroacetic acid to provide carboxylic acid (xvii). The carboxylic acid (xvii) was converted to the hydroxamate (xviii) following the procedure outlined in Scheme 1. Hydrogenation of (xvii) in the prescence of a palladium catalyst provided a compound of formula I.