Reacción #803427

Ecuación de reacción

Methyl 6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazine-3-carboxylate

MeOH

lithium aluminum hydride

NaH

→

title compound

Rendimiento 96.4%

3-(hydroxymethyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-6(6aH)-one

Rendimiento 96.4%

Disolventes

tetrahydrofuran

water

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction was stirred at a temperature between −20 and −10° C. for 1 h
2. 2
   TemperaturaThe reaction was then cooled back to −60° 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
   Filtraciónfiltered through a medium frit
7. 7
   OtroThe layers were separated
8. 8
   Extracciónthe aqueous phase was extracted with ethyl acetate (3×100 mL)
9. 9
   Lavadowashed with brine (100 mL)
10. 10
    Secadodried with sodium sulfate
11. 11
    Concentraciónconcentrated

Procedimiento

Methyl 6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazine-3-carboxylate (500 mg, 1.91 mmol) was taken up in tetrahydrofuran (23 mL) in an inert environment. To the stirred suspension at room temperature was added NaH (60% dispersion in mineral oil, 114.7 mg, 2.87 mmol) and stirred 30 min. The reaction was then cooled to −45° C. and lithium aluminum hydride (2M in THF, 1.91 mL, 3.82 mmol) was added. The reaction was stirred at a temperature between −20 and −10° C. for 1 h. The reaction was then cooled back to −60° 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 (300 mL) and water (200 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 (3×100 mL). The organic layers were combined, washed with brine (100 mL), dried with sodium sulfate and concentrated to yield the title compound (429.4 mg, 96%) as a white solid. [M+H] calc'd for C12H15N3O2, 234. found, 234.

Fuente