HCID 242258, compound → Tricyclo(5.2.1.0,2,6)decan-8-amine

2.2 g of 1,3a,4,6,7,7a-hexahydro-4,7-methanoinden-5-one oxime were dissolved in 50 ml of methanol, and about 10% Raney nickel, dissolved in 50% water, was added. The mixture was hydrogenated at 100 bar and 100° C. for 20 hours, the catalyst was then filtered off, and the solvent was evaporated under reduced pressure. The residue was taken up in ether and 6 N aqueous sodium hydroxide solution, the phases were separated, the aqueous phase was extracted three times with ether, the combined organic phases were dried with magnesium sulfate and filtered, and the filtrate was concentrated. This gave 1.8 g of a colorless oil which was purified by kugelrohr distillation. This gave 0.96 g of the desired amine as an oil.

1. additionwas added
2. filtrationthe catalyst was then filtered off
3. customthe solvent was evaporated under reduced pressure
4. custom6 N aqueous sodium hydroxide solution, the phases were separated
5. extractionthe aqueous phase was extracted three times with ether
6. dry with materialthe combined organic phases were dried with magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate was concentrated
9. distillationThis gave 1.8 g of a colorless oil which was purified by kugelrohr distillation

ORD record

ord-a5c67892925548bbac54c7dace066cc8

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825231B2