Reaktion #443861

Reaktionsgleichung

methanol

cis-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine

trifluoroacetic acid

→

title compound

Ausbeute 94.0%

cis-4-Benzylamino-3-fluoropiperidine

Ausbeute 94.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvents were removed in vacuo
2. 2
   workup.ADDITIONMore methanol (2 mL) was added
3. 3
   Sonstigeremoved in vacuo
4. 4
   SonstigeThe residue was partitioned between CH2Cl2 (30 mL) and dilute NaOH solution (20 mL)
5. 5
   ExtraktionThe aqueous layer was further extracted with CH2Cl (30 ml×2)
6. 6
   Waschenthe combined organic extracts were washed with brine (50 mL)
7. 7
   Trocknendried (Na2SO4)
8. 8
   Sonstigeevaporated in vacuo

Vorschrift

To a solution of cis-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine (0.9087 g, 2.95 mmol) in anhydrous dichloromethane (5 mL) under argon was added trifluoroacetic acid (2.5 mL) and the solution was stirred at room temperature under argon for 140 min. Anhydrous methanol (1 mL) was added and the solvents were removed in vacuo. More methanol (2 mL) was added and removed in vacuo. The residue was partitioned between CH2Cl2 (30 mL) and dilute NaOH solution (20 mL). The aqueous layer was further extracted with CH2Cl (30 ml×2) and the combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and evaporated in vacuo to give 0.5756 g (94%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.54 (1H, qd, J=12.0 and 4.1 Hz), 1.83 (1H, m), 2.54-2.76 (3H, m), 3.11 (1H, m), 3.88 (2H, m), 4.73 (1H, m), 7.23-7.37 (5H, m).

Quelle