Ammonium formate → Methyl 4-aminoadamantane-1-carboxylate

4-Oxo-adamantane-1-carboxylic acid methyl ester (6.5 g, 31.2 mmol) (prepared following J. Org. Chem. 1983, 48, 1101) was dissolved in MeOH (75 ml). To this solution was added 10% Pd—C (1 g) followed by ammonium formate (10 g, 158 mmol). The reaction mixture was heated under reflux for 1 h after which it was cooled to ambient temperature and filtered through hyflo bed. The clear filtrate was concentrated under reduced pressure, and the residue was diluted with water and extracted with EtOAc. The aqueous layer was separated, basified with 10% NaOH solution and extracted with EtOAc. The combined organic layer was dried over anhydrous sodium sulphate and solvent removed under reduced pressure to give 4-aminoadamantane-1-carboxylic acid methyl ester (5 g, 77%). LC-MS (m/z): 210 (M+1). 1H NMR (300 MHz, DMSO-d6): δ 3.6 (s, 3H), 3.2 (d, 1H), 1.4-2.2 (13H, m).

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 1 h after which it
3. filtrationfiltered through hyflo bed
4. concentrationThe clear filtrate was concentrated under reduced pressure
5. additionthe residue was diluted with water
6. extractionextracted with EtOAc
7. customThe aqueous layer was separated
8. extractionextracted with EtOAc
9. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate and solvent
10. customremoved under reduced pressure

ORD record

ord-6be1e11ac931435f9faad664fb036a0e

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334305B2