Reaktion #84690

Reaktionsgleichung

trans-tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate

triethyl amine

N-(benzyloxycarbonyloxy)succinimide

→

title compound

Ausbeute 100.0%

trans-tert-butyl 4-(benzyloxycarbonylamino)-3-hydroxypiperidine-1-carboxylate

Ausbeute 100.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe solution mixture was washed with 5% citric acid solution (2×100 mL), 5% potassium carbonate solution (2×100 mL) and brine (200 mL)
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenfollowed by concentration under reduced pressure
5. 5
   SonstigeThe resultant oily matter was purified by silica gel column chromatography (ethyl acetate: petroleum ether=1:4˜1:2)

Vorschrift

To a stirred mixture of trans-tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate (1.05 g, 4.86 mmol) in 80 mL of dichloromethane was added triethyl amine (5.89 g, 5.83 mmol), followed by the addition of N-(benzyloxycarbonyloxy)succinimide (1.27 g, 5.10 mmol) at 0° C. The reaction was stirred at room temperature for 16 hours and then diluted with 100 mL of dichloromethane. The solution mixture was washed with 5% citric acid solution (2×100 mL), 5% potassium carbonate solution (2×100 mL) and brine (200 mL). The organic layer was dried over anhydrous sodium sulfate and filtered, followed by concentration under reduced pressure. The resultant oily matter was purified by silica gel column chromatography (ethyl acetate: petroleum ether=1:4˜1:2) to afford the title compound (1.7 g, ˜100%, crude) as a colorless oil. MS (ES+) C18H26N2O5 requires: 350, found: 251 [M+H−100]+.

Quelle