Reaktion #48378

Reaktionsgleichung

Sodium triacetoxyborohydride

acetic acid

N-Boc-3-amino-4-pyridine carboxaldehyde

ethyl 4-aminopiperidine-1-carboxylate

dichloroethane

→

title compound

Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with saturated aqueous sodium bicarbonate
2. 2
   SonstigeThis was separated
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   Trocknenthe combined organics were dried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give the crude product
8. 8
   SonstigeThis was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which

Vorschrift

Sodium triacetoxyborohydride (0.57 g, 2.70 mmol) and acetic acid (0.41, 6.75 mmol) were added to a solution of N-Boc-3-amino-4-pyridine carboxaldehyde (0.50 g, 2.25 mmol) and ethyl 4-aminopiperidine-1-carboxylate (0.47 g, 2.70 mmol) in dichloroethane (5 mL) at room temperature. The reaction was stirred overnight, and quenched with saturated aqueous sodium bicarbonate. This was separated, extracted with ethyl acetate and the combined organics were dried over sodium sulfate. The solution was filtered and evaporated to give the crude product. This was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.47 g). MS 379.3.

Quelle