Acetone → HCID 19774271, compound

Participants

Reaction Steps

Compound (XXI) (0.75 g) was combined with NaBH4 (0.14 g) in MeOH (30 ml) and stirred at ambient temperature for 31/2 hours. A further 0.14 g NaBH4 was added and the reaction was stirred a further 1/2 hour. Acetone (10 ml) was added. After stirring 18 hours, the solvent was evaporated and the residue was partitioned between EtOAc and aqueous NaHCO3. The EtOAc was evaporated, and the residue was chromatographed on a silica column, eluting the product with CH2Cl2 /MeOH as a gummy solid (0.5 g). This was converted to its HCl salt using EtOH/concentrated HCl and recrystallized from EtOH to yield Compound XXII.HCl (0.2 g), m.p. 214°-220° (dec.). The elemental analysis for C, H, and N and mass spectra were consistent with the structure indicated. The NMR spectrum suggested that the 1,2-trans-isomer was the principal constituent, though some of the 1,2-cis-isomer was present also.

Provenance & Evidence