Diethyl Ether → HCID 131716321, compound

Participants

Reaction Steps

A solution of 3.00 g (6.09 mmol) of the title compound from Example 23 in 200 ml of ethanol was treated with 0.30 g of PtO2 and placed on the Parr apparatus under 50 psi of hydrogen for 2 hours. TLC at this point indicated the reduction of the pyridyl group was complete. The catalyst was filtered under nitrogen and solvent evaporated to give a solid residue. The latter was dissolved in 30 ml of CH3CN and luted with 330 ml of ether to give a solid. This mixture was cooled overnight and filtered to give 1.29 g (43%) of Isomer A, m.p. 177°-180° C. (s. 160° C.). Isomer A was dissolved in 20 ml of hot isopropyl alcohol, filtered through filter cel (to remove trace of catalyst), cooled overnight and filtered to give 0.72 g of nearly colorless solid, [α]D +112°, (c=1.0 MeOH). After recrystallization from 18 ml of hot isopropyl alcohol, the product weighed 0.63 g (21%); m.p. 177°-180° C. (s. 160° C.); [α]D +113° C. (c=1.0, MeOH); Rf 0.59 (80:20 CH2Cl2 -MeOH).

Provenance & Evidence