Salicylic Acid → 3-Aminoquinuclidine

Participants

Reaction Steps

A solution of salicylic acid (3.46 g, 25 mmole) in anhydrous tetrahydrofuran (20 ml) under nitrogen is treated with 1,1'-carbonyldiimidazole (4.22 g, 26 mmole), stirred for one hour, then degassed with a stream of nitrogen. A solution of 3-aminoquinuclidine (from 30 mmole of dihydrochloride) in tetrahydrofuran (10 ml) is prepared, and the solution is added dropwise to the first solution. After 18 hours at room temperature, the reaction mixture is concentrated in vacuo and partitioned between methylene chloride (200 ml) and water (100 ml). The resultant organic layer is separated and the aqueous solution is extracted with methylene chloride (100 ml). The combined organic solutions are dried (Na2SO4), concentrated in vacuo, and passed through a short column of alumina (eluted first with 5% methanol/tetrahydrofuran, then with 25% methanol/tetrahydrofuran) to provide 3.20 g (52%) of product as a colorless foam.

Provenance & Evidence