Reaktion #48367

Reaktionsgleichung

Sodium triacetoxyborohydride

2,3-diamino-6-methoxypyridine

N-(t-butoxycarbonyl)-4-piperidone

→

title compound

2-Amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino)-6-methoxypyridine

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water (50 mL)
2. 2
   Extraktionextracted with chloroform
3. 3
   Waschenwashed with 5% aqueous sodium hydroxide, water and saturated sodium chloride solution
4. 4
   TrocknenAfter drying 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, where the more polar product
9. 9
   Sonstigewas isolated (silica gel, 50% ethyl acetate hexane, Rf=0.36)

Vorschrift

Sodium triacetoxyborohydride (3.39 g, 16.0 mmol) was added to a solution of 2,3-diamino-6-methoxypyridine (2.23 g, 16.0 mmol) and N-(t-butoxycarbonyl)-4-piperidone (7.66 g, 38.4 mmol) in dichloroethane (50 mL) at room temperature. The reaction was quenched with water (50 mL) and stirred overnight, then extracted with chloroform and washed with 5% aqueous sodium hydroxide, water and saturated sodium chloride solution. After drying over sodium sulfate, the solution was filtered and evaporated to give the crude product. This was purified by chromatography, where the more polar product was isolated (silica gel, 50% ethyl acetate hexane, Rf=0.36), to give the title compound. MS 323 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.99 (d, J=8 Hz, 1H), 6.05 (d, J=8 Hz, 1H), 4.45 (br s), 4.03 (br s), 3.83 (s, 3H), 3.15 (m, 1H), 2.86 (m, 2H), 1.91 (d, J=12 Hz, 2H), 1.5 (br s, 11H), 1.26 (br s, 2H).

Quelle