Citric Acid → HCID 21478765, compound

Participants

Reaction Steps

To a solution of sodium dihydrogenphospate (123.1 g) and citric acid (31.1 g) in water (3000 ml) were added in turn n-butylamine (35.5 g) and acetonedicarboxylic acid (77.0 g) and pH was adjusted to 4.6 with a 10% aqueous solution of sodium hydroxide. To the reaction solution was added dropwise at room temperature a solution of the crude aldehyde (23 g) in methanol (20 ml) and the mixture was stirred for 65 hours. Then, a 10% aqueous solution of potassium hydroxide (300 ml) was added to the reaction solution and extracted five times with chloroform. The combined organic layer was washed with a 10% aqueous solution of sodium hydroxide (200 ml), dried over potassium carbonate and the solvent was distilled off under reduced pressure. The residue was purified by a silica gel column chromatography (ethyl acetate) to give 9-(n-butyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one (28.2 g).

Provenance & Evidence