1-Chloroethyl chloroformate → 8-Azabicyclo[3.2.1]octane hydrochloride

Temperature

120 °C

To an oven-dried, 100-mL, round-bottomed flask was added tropane (2.5 g, 19.96 mmol) followed by toluene (20 mL), and a-chloro-ethyl chloroformate (3.2 mL, 30 mmol). The flask was purged with N2 and the mixture was heated at 120° C. for 16 h. The reaction was allowed to cool to room temperature and the solvent was evaporated in vacuo. The resulting residue was dissolved in MeOH (20 mL) and heated to reflux at 85° C. for 3 h. The solvent was evaporated in vacuo and the product dried under vacuum to give 2.90 g (98% yield) of a light brown solid. MS m/z: 112.0 (M+1). 1H NMR (DMSO-d6; 400 MHz): d 1.64 (m, 4), 1.95 (m, 6), 3.92, (s, 2), 9.24 (br d, 2, J=7.3).

1. customThe flask was purged with N2
2. temperatureto cool to room temperature
3. customthe solvent was evaporated in vacuo
4. dissolutionThe resulting residue was dissolved in MeOH (20 mL)
5. temperatureheated
6. temperatureto reflux at 85° C. for 3 h
7. customThe solvent was evaporated in vacuo
8. customthe product dried under vacuum

ORD record

ord-4c1975f272a748afae93468a11dfd09a

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06583154B1