TERT-BUTYL 4-AMINO-3-FLUOROPIPERIDINE-1-CARBOXYLATE Chemical Properties

Boiling point:

285.6±40.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

8.88±0.40(Predicted)

Appearance

Off-white to light yellow Solid-liquid mixture

TERT-BUTYL 4-AMINO-3-FLUOROPIPERIDINE-1-CARBOXYLATE Usage And Synthesis

Uses

1-(tert-Butyloxycarbonyl)-3-Fluoro-4-aminopiperidine is a reactant in the preparation of pharmaceutical compounds which are antagonists of CGRP (Calcitonin gene-related peptide) receptors and useful in the treatment of migraine.

Synthesis

At room temperature, tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (5.10 g, 23.02 mmol) was dissolved in methanol (100 mL), and ammonium acetate (12.51 g, 162.29 mmol) and sodium cyanoborohydride (1.90 g, 29.92 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the reaction was quenched with 1% aqueous sodium carbonate (50 mL). The reaction mixture was extracted with ethyl acetate (100 mL × 3) and the organic layers were combined and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to afford tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate as a yellow solid (4.9 g, 98% yield).

References

[1] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 0428; 0429
[2] Patent: US2015/51209, 2015, A1
[3] Patent: WO2015/22662, 2015, A1

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