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

HRID 406208

Reaction equation

HRID 406208 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-ba3f6fb4214f4382b6814a3ccf8c095f
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Linked notes

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