Réaction #992739

Équation de réaction

rac-{1-[2-(7-fluoro-2-methoxy-quinolin-8-yl) -3-hydroxy-propyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

→

amine

Rendement 100.6%

rac-3-(4-amino-piperidin-1-yl)-2-(7-fluoro-2-methoxy-quinolin-8-yl)-propan-1-ol

Rendement 100.6%

Solvants

TFA

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was removed in vacuo
2. 2
   workup.ADDITIONthe residue was diluted in sat. NaHCO3 (20 mL)
3. 3
   ExtractionThe aq. layer was extracted 3 times with DCM-MeOH (9-1, 3×25 mL)
4. 4
   Lavagelayers were washed once with brine (20 mL)
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated to dryness

Mode opératoire

A solution of rac-{1-[2-(7-fluoro-2-methoxy-quinolin-8-yl) -3-hydroxy-propyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (WO 2007/081597, 1.42 g, 3.28 mmol) in a mixture of TFA (15 mL) and DCM (9 mL) was stirred at rt for 20 min. The solvent was removed in vacuo and the residue was diluted in sat. NaHCO3 (20 mL). The pH was adjusted to 12 adding 6M NaOH. The aq. layer was extracted 3 times with DCM-MeOH (9-1, 3×25 mL). The combined org. layers were washed once with brine (20 mL), dried over Na2SO4, filtered and concentrated to dryness to afford the title amine as a yellowish gum (1.1 g, 100% yield).

Source