Salicylic Acid → 3-Aminoquinuclidine

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.

1. customdegassed with a stream of nitrogen
2. additionthe solution is added dropwise to the first solution
3. waitAfter 18 hours at room temperature
4. concentrationthe reaction mixture is concentrated in vacuo
5. custompartitioned between methylene chloride (200 ml) and water (100 ml)
6. customThe resultant organic layer is separated
7. extractionthe aqueous solution is extracted with methylene chloride (100 ml)
8. dry with materialThe combined organic solutions are dried (Na2SO4)
9. concentrationconcentrated in vacuo
10. washeluted first with 5% methanol/tetrahydrofuran

ORD record

ord-e5456af33b2741fcb23d168fa9ffe97d

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05084460