반응 #48376

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Sodium triacetoxyborohydride

acetic acid

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

ethyl 4-aminopiperidine-1-carboxylate

dichloroethane

→

title compound

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

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후처리

1. 1
   기타quenched with saturated aqueous sodium bicarbonate
2. 2
   기타This was separated
3. 3
   추출extracted with ethyl acetate
4. 4
   건조the combined organics were dried over sodium sulfate
5. 5
   여과The solution was filtered
6. 6
   기타evaporated
7. 7
   기타to give the crude product
8. 8
   기타This was purified by chromatography (silica gel, 0 to 12% methanol in methylene chloride gradient elution), which

실험 절차

Sodium triacetoxyborohydride (1.70 g, 8.03 mmol) and acetic acid (0.29, 4.82 mmol) were added to a solution of N-Boc-4-amino-3-pyridine carboxaldehyde (0.36 g, 1.61 mmol) and ethyl 4-aminopiperidine-1-carboxylate (0.33 g, 1.93 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, 0 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.24 g). MS 379.2.

출처