Réaction #1840360

Équation de réaction

7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one

cyclohexanone

acetic acid

cyclohexanone

acetic acid

sodium triacetoxyborohydride

→

7-(cyclohexylamino)-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   AutreThe mixture was quenched with a saturated aqueous solution of NaHCO3
3. 3
   workup.ADDITIONAdditional CH2Cl2 (3 mL) was added
4. 4
   Autrethe organic layer separated
5. 5
   Extractionthe aqueous layer was further extracted with CH2Cl2 (3 mL)
6. 6
   SéchageThe organic layers were combined dried (Na2SO4)
7. 7
   Filtrationfiltrated
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Autreto give a residue that
10. 10
    Autrewas purified by flash chromatography (Biotage SP4, gradient 0-10% MeOH in EtOAc)

Mode opératoire

To a solution of 7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one (33 mg, 0.081 mmol) in CH2Cl2 (0.5 mL) was added cyclohexanone (9 μL, 0.081 mmol), acetic acid (7 μL, 0.12 mmol) followed by sodium triacetoxyborohydride (26 mg, 0.12 mmol). After stirring the mixture for three further hours, cyclohexanone (20 μL, 0.18 mmol) was added followed by the addition of additional acetic acid (20 μL, 0.34 mmol). The mixture was quenched with a saturated aqueous solution of NaHCO3. Additional CH2Cl2 (3 mL) was added and the organic layer separated, the aqueous layer was further extracted with CH2Cl2 (3 mL). The organic layers were combined dried (Na2SO4), filtrated, concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4, gradient 0-10% MeOH in EtOAc) and reverse phase chromatography (Biotage SP4, 12 g C18 cartridge; gradient ACN in water). The compound 7-(cyclohexylamino)-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (112) was isolated as a solid (1.6 mg, yield 1%).

Source