反応 #605116

反応方程式

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

溶媒

Water

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued at room temperature overnight
3. 3
   その他was separated
4. 4
   その他dried
5. 5
   その他separating column
6. 6
   その他The solvent was removed under reduced pressure
7. 7
   その他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
8. 8
   workup.WAITto stand at room temperature for 2 days
9. 9
   ろ過The resulting suspension was collected by filtration
10. 10
    その他dried in a vacuum oven
11. 11
    その他The crude material was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

実験手順

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;

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