Reacción #605116

Ecuación de reacción

sodium triacetoxyborohydride

Hex-5-enal

2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Intermediate B

2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

→

title compound

5-(Hex-5-enyl)-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued at room temperature overnight
3. 3
   Otrowas separated
4. 4
   Otrodried
5. 5
   Otroseparating column
6. 6
   OtroThe solvent was removed under reduced pressure
7. 7
   Otrothe resulting brown oil was purified by flash column chromatography on silica eluting with 0-100% EtOAc in iso-hexane on a 80 g silca cartridge
8. 8
   workup.WAITto stand at room temperature for 2 days
9. 9
   FiltraciónThe resulting suspension was collected by filtration
10. 10
    Otrodried in a vacuum oven
11. 11
    OtroThe crude material was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Procedimiento

Hex-5-enal (step 1) (solution in DCM, 25 mmol) was treated with 2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate B) (3.94 g, 12.5 mmol). After stirring at room temp under nitrogen for 30 mins, sodium triacetoxyborohydride (3.18 g, 15.00 mmol) was added and stirring continued at room temperature overnight. Water (100 ml) was added to the reaction mixture. Once effervescence had ceased the organic portion was separated and dried by passing through a phase separating column. The solvent was removed under reduced pressure and the resulting brown oil was purified by flash column chromatography on silica eluting with 0-100% EtOAc in iso-hexane on a 80 g silca cartridge. The combined fractions were allowed to stand at room temperature for 2 days. The resulting suspension was collected by filtration and dried in a vacuum oven. The crude material was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound;

Fuente