Hydrochloric Acid → HCID 86657810, compound

To a solution of (±)-trans-4-difluoromethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (1.52 mmol, 0.45 g) in DCM (2 mL) was added 4 N HCl in dioxane (3 mL). The solution was stirred for 1 hour. The solvents were removed with reduced pressure. The crude amine hydrochloride was dissolved in DCM (3 mL), and saturated NaHCO3 (3 mL). To this suspension was added di-tert-butyl carbonate (4.12 mmol, 0.90 g) and the reaction was stirred for 30 minutes at room temperature. The layers were separated and the DCM layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified on a 12 g SiO2 cartridge using a 0-30% ethyl acetate/hexanes gradient to give (±)-trans-4-difluoromethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.14 g).

1. customThe solvents were removed with reduced pressure
2. dissolutionThe crude amine hydrochloride was dissolved in DCM (3 mL)
3. stirringthe reaction was stirred for 30 minutes at room temperature
4. customThe layers were separated
5. dry with materialthe DCM layer was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified on a 12 g SiO2 cartridge

ORD record

ord-8c40238d453b42c6acd8db4a089f200a

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741900B2