Reaktion #168295

Reaktionsgleichung

tert-butyl-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate

tert-butyl-3-(benzylamino)-4-hydroxypiperidine-1-carboxylate

triethylamine

chloroacetyl chloride

→

tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched with water (300 mL) at 0° C.
2. 2
   Extraktionextracted with DCM (500 mL×3)
3. 3
   WaschenThe organic layer was washed with brine (1 L)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel chromatography

Vorschrift

To a solution of tert-butyl-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate and tert-butyl-3-(benzylamino)-4-hydroxypiperidine-1-carboxylate (153 g, 0.42 mol, crude) and triethylamine (126 g, 1.25 mol) in DCM (800 mL) was added drop wise chloroacetyl chloride (33 g, 0.45 mol) at room temperature. The mixture was stirred at room temperature overnight. The mixture was quenched with water (300 mL) at 0° C., and extracted with DCM (500 mL×3). The organic layer was washed with brine (1 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate as a mixture of trans diastereomers which was used directly in the next step.

Quelle