2,2,2-Trifluoroethyl trifluoromethanesulfonate → Racemic [1-(2,2,2-trifluoro-ethyl)-piperidin-3-yl]-carbamic acid tert-butyl ester

Temperature

50 °C

Trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (0.42 g, 1.8 mmol) was dissolved in a mixture of 1.5 mL of EtOAc and 1.5 mL of H2O containing 0.95 g of NaHCO3 (7.5 mmol). The resulting suspension was warmed to 50 C. A solution of racemic piperidin-3-yl-carbamic acid tert-butyl ester (0.30 g, 1.5 mmol) in 1 mL of EtOAc was added dropwise over a 30 minute period. The reaction mixture was left stirring at 50° C. for one hour before being cooled to RT. The organic phase was separated and the aqueous layer was back extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and evaporated to give 0.38 g of racemic [1-(2,2,2-trifluoro-ethyl)-piperidin-3-yl]-carbamic acid tert-butyl ester as a colorless oil which was used in the next step without purification.

1. temperatureThe resulting suspension was warmed to 50 C
2. waitThe reaction mixture was left
3. temperaturebefore being cooled to RT
4. customThe organic phase was separated
5. extractionthe aqueous layer was back extracted with EtOAc
6. washThe combined organics were washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customevaporated

ORD record

ord-bd2870a6a5eb426c925084b207db4d99

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012974B2