Sulfuric Acid → 1-Methoxytricyclo[3.3.1.03,7]nonan-3-amine

To the suspension of 1-methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid obtained from step IV (0.39 g, 2.0 mmol) in CHCl3 (10 mL) was added conc. H2SO4 (1.0 mL, 20 mmol). Solid NaN3 (0.39 g, 6.0 mmol) was added in portions by keeping the reaction temperature below 40° C. After stirring at room temperature for 2 hrs, the reaction mixture was cooled to ice bath temperature, diluted with water and extracted with EtOAc. The aqueous layer was basified by adding 50% NaOH solution and extracted with CHCl3. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-methoxytricyclo[3.3.1.03,7]nonan-3-amine (0.23 g) in 69% yield. m/z (M+1) 168; 1H NMR (CDCl3) 300 MHz δ 3.27 (s, 3H), 2.40-2.34 (m, 1H), 2.16-2.08 (m, 1H), 1.97 (ddd, J=2.0, 6.8, 8.7 Hz, 1H), 1.92-1.53 (m, 7H), 1.51-1.38 (m, 2H).

1. customthe reaction temperature below 40° C
2. temperaturethe reaction mixture was cooled to ice bath temperature
3. extractionextracted with EtOAc
4. additionby adding 50% NaOH solution
5. extractionextracted with CHCl3
6. washThe combined organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. customthe solvent was removed under reduced pressure

ORD record

ord-5fb4344bbf1e4bc58428c68708c3e7ad

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985759B2