Reaktion #84693

Reaktionsgleichung

trans-tert-butyl 3-azido-4-(benzyloxycarbonylamino)piperidine-1-carboxylate

triphenylphosphine

→

trans-tert-butyl 3-amino-4-(benzyloxycarbonylamino)piperidine-1-carboxylate

Ausbeute 44.7%

Lösungsmittel

THF

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   WaschenThe organic layer was washed with brine (50 mL)
3. 3
   Sonstigedirectly evaporated under reduced pressure
4. 4
   SonstigeThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1˜1:1)

Vorschrift

A mixture of crude trans-tert-butyl 3-azido-4-(benzyloxycarbonylamino)piperidine-1-carboxylate (12 g, ˜32 mmol) and triphenylphosphine (41.9 g, 160 mmol) in THF (100 mL) and water (5 mL) was stirred at 70° C. for 2 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (500 mL). The organic layer was washed with brine (50 mL) and directly evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1˜1:1) to afford trans-tert-butyl 3-amino-4-(benzyloxycarbonylamino)piperidine-1-carboxylate (5.0 g, 44%) as a yellow oil. MS (ES+) C18H27N3O4 requires: 349, found: 350 [M+H]+.

Quelle