Solid-phase reagents for the isolation and protection of carbonyl compounds

Resins which can serve as solid-phase Girard reagents have been prepared. These consist of porous cross-linked polystyrene-divinylbenzene matrices functionalized either with acid hydrazide groups, 1 or with O-alkylhydroxylamine groups, 2. Both resins react rapidly, under acid catalysis, with steroidal ketones and with glucose to form resin bound carbonyl derivatives. The carbonyl compound can be recovered by exchange with acetone under mildly acidic conditions. Resin 2 was used to extract steroidal ketones from an extract of bovine adrenals. By protecting the C-20 ketone group of allopregnanolone, resin 2 was used to prepare the counterpart of the steroid bearing tritium in the 3 alpha-position.