Butylamine → N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (10 grams), methanol (80 ml), n-butyl amine (20 ml) and potassium carbonate (10.6 grams) was heated to 40-45° C. and stirred up to completion of the reaction. The reaction mixture was distilled under reduced pressure and methylene chloride (100 ml) was added to the obtained residue at 25-30° C. and stirred for 15 minutes. The unwanted solid was filtered off and the filtrate was distilled off under reduced pressure. The obtained residue was dissolved in methylene chloride (32 ml) and a mixture of TEMPO (0.015 grams), potassium bromide (0.36 grams) in methylene chloride (48 ml) was added to it and stirred for 15 minutes. Sodium hypochlorite solution (20.8 ml) was added to the reaction mixture at −15 to 15° C. and stirred for an hour. After completion of the reaction, the reaction mixture was quenched with sodium thio sulfate solution at below 10° C. Both organic and aqueous layers were separated and aqueous layer extracted with methylene chloride. The solvent from organic layer was distilled off under reduced pressure to get the title compound.

Provenance & Evidence