Water → 5-(Pent-4-enyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

HRID 2276551Notes

Reaction equation

HRID 2276551 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][NH:16][C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:23](=O)[CH2:24][CH2:25][CH:26]=[CH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH2:27]([N:16]1[C:10]2[C:11](=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:9]=2)[CH2:13][CH2:14][CH2:15]1)[CH2:26][CH2:25][CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 962WaterHCID 164184-PentenalHCID 5049666Sodium triacetoxyborohydrideHCID 666655612,3-Diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

Product 1

HCID 666663485-(Pent-4-enyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine (Ex. 4.1 step 1) (2 g, 6.96 mmol) in DCE (35 ml) was added pent-4-enal (2.061 ml, 20.88 mmol) and the mixture was stirred at RT overnight. A further portion of sodium triacetoxyborohydride (4.43 g, 20.88 mmol) was added and the mixture was stirred at RT for 2.5 hours under an atmosphere of nitrogen. Water was added and the mixture was extracted with EtOAc (3×60 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by chromatography on silica eluting with EtOAc/iso-hexane to afford the title compound;

Workup

  1. stirringthe mixture was stirred at RT for 2.5 hours under an atmosphere of nitrogen
  2. extractionthe mixture was extracted with EtOAc (3×60 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by chromatography on silica eluting with EtOAc/iso-hexane

Sources & evidence

ORD record
ord-c30e8c7edc2d4a38925f74f154c77acf
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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