Reaction #1121812

Reaction equation

tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

triethylamine trihydrofluoride

sodium bicarbonate

DCM

→

trans-tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate

Yield 58.3%

Solvents

DCE

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   OtherThe organic phase was separated
3. 3
   Washwashed with brine
4. 4
   Dryingdried (sodium sulfate)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe residue obtained
7. 7
   Otherwas purified by flash chromatography on silica gel (hexane:ethyl acetate 1:1)

Procedure

A mixture of tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (5.46 g, 27.4 mmol) and triethylamine trihydrofluoride (4.42 g, 27.4 mmol) in DCE (4 mL) was stirred at 80° C. (bath) for 18 hours. After cooling to room temperature, saturated sodium bicarbonate (20 mL) and DCM (30 mL) were added. The organic phase was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (hexane:ethyl acetate 1:1) to give trans-tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate (3.5 g, 58%) as a solid.

Source