반응 #156831

반응 방정식

Methyl 4-benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate

MeOH

lithium aluminum hydride

NaH

→

title compound

수율 99.3%

4-benzyl-7-(hydroxymethyl)-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

수율 99.3%

용매

tetrahydrofuran

water

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred at a temperature between −20 and −10° C. for 2 h
2. 2
   온도The reaction was then cooled back to −78° C.
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGto stir at ambient temperature for 2 h
5. 5
   workup.STIRRINGThe biphasic mixture was stirred vigorously
6. 6
   여과filtered through a medium frit
7. 7
   기타The layers were separated
8. 8
   추출the aqueous phase was extracted with ethyl acetate (2×50 mL)
9. 9
   세척washed with brine (100 mL)
10. 10
    건조dried with sodium sulfate
11. 11
    농축concentrated

실험 절차

Methyl 4-benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate (600 mg, 2.02 mmol) was taken up in tetrahydrofuran (25 mL) in an inert environment. To the stirred suspension at room temperature was added NaH (60% dispersion in mineral oil, 121 mg, 3.03 mmo) and stirred 30 min. The reaction was then cooled to −78° C. and lithium aluminum hydride (3 mL, 2M in THF) was added. The reaction was stirred at a temperature between −20 and −10° C. for 2 h. The reaction was then cooled back to −78° C. and MeOH (1 mL) followed by water (1 mL) was added. The reaction was allowed to stir at ambient temperature for 2 h and then poured into ethyl acetate (200 mL) and water (100 mL). The biphasic mixture was stirred vigorously and then filtered through a medium frit. The layers were separated and the aqueous phase was extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine (100 mL), dried with sodium sulfate and concentrated to afford the title compound (540 mg, 99%) as a white solid. [M+H] calc'd for C15H15N3O2, 270; found, 270.

출처