Acetic Acid → HCID 60026333, compound

Participants

Reaction Steps

To a solution of the aldehyde of Example 94 (0.050 g, 0.107 mmol) and 0.078 mL of acetic acid in 3.0 mL of dichloroethane was added morpholine (0.233 mL, 2.68 mmol) at 0° C. The reaction was allowed to stir at room temperature for 30 minutes. To this yellow solution was added triacetoxy sodium borohydride (0.057 mg, 0.268 mmol), then continued stirring at room temperature for 14 hours. The reaction mixture was diluted with 10 mL of ethyl acetate and 2 mL of 3% ammonium hydroxide solution. The biphasic system was separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with three 20 mL portions of water, brine, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo to give yellow oil. This crude material was applied onto a flash column and eluted with 5% MeOH—CH2Cl2, 0.5% NH4OH, to give the title compound (0.018 g, 32.0% yield) as a white foam.

Provenance & Evidence