Ethyl Acetate → 2-(Adamantan-1-yl)-N-methylethan-1-amine

A solution of 1-adamantaneacetic acid N-methylamide (1.54 g, 7.45 mmol) in tetrahydrofuran (15.0 ml) was added dropwise to a solution of lithium aluminum hydride (569 mg, 15.0 mmol) in diethyl ether (34.0 ml) under ice-cooling over five minutes. The mixture was refluxed for six hours and then stirred under ice-cooling again. Ethyl acetate was added to the reaction mixture to treat excess lithium aluminum hydride, and then the whole was extracted with 1 N hydrochloric acid (50 ml) twice. A 4 N aqueous sodium hydroxide solution was added to the extract to basify it, and the whole was extracted with diethyl ether (80 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (60 ml) and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 890 mg (66%) of the titled compound.

1. temperaturecooling over five minutes
2. temperatureThe mixture was refluxed for six hours
3. temperaturecooling again
4. extractionthe whole was extracted with 1 N hydrochloric acid (50 ml) twice
5. additionA 4 N aqueous sodium hydroxide solution was added to the
6. extractionextract
7. extractionthe whole was extracted with diethyl ether (80 ml)
8. washThe organic layer was washed with a saturated aqueous sodium chloride solution (60 ml)
9. dry with materialdried over magnesium sulfate
10. customThe solvent was evaporated under reduced pressure

ORD record

ord-77e4a237654146e5910d99caf230f57d

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098226B2