Hydrogen Peroxide → ethyl 7-(7-hydroxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 406233Notes

Reaction equation

HRID 406233 reaction equation
B.C1C[O:5]CC1.C1COCC1.[C:12]1([CH3:46])[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[C:20]3[CH:34]=[CH:33][CH2:32][N:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:21]3=[N:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[CH:14][CH:13]=1.OO.[OH-].[Na+]>>[OH:5][CH:33]1[CH2:32][N:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:21]2=[N:22][C:23]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([CH3:46])=[CH:17][CH:16]=3)[N:19]=[C:20]2[CH2:34]1

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 66665938Ethyl 7-(2,3-dip-tolylpyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 66665937ethyl 7-(7-hydroxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Procedure

A solution of 1M BH3.THF in THF (3.66 ml, 3.66 mmol) was added dropwise to Ethyl 7-(2,3-dip-tolylpyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (1.145 g, 2.438 mmol) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 1 hour and then cooled to 0-5° C. using an ice bath. The mixture was treated with 35% H2O2 (1.067 ml, 12.19 mmol) followed by 2M NaOH (6.10 ml, 12.19 mmol). The mixture was allowed to warm to room temperature and stirred overnight under an atmosphere of nitrogen. The reaction mixture was washed with water (25 ml) and extracted with ethyl acetate (2×25 ml). The organic extracts were combined, dried over MgSO4, filtered and the filtrate concentrated in vacuo to give an orange oil. The crude product was purified by chromatography on silica eluting with EtOAc/iso-hexane, followed by further purification by chromatography on silica eluting with DCM/MeOH to afford the title compound;

Workup

  1. temperaturecooled to 0-5° C.
  2. temperatureto warm to room temperature
  3. stirringstirred overnight under an atmosphere of nitrogen
  4. washThe reaction mixture was washed with water (25 ml)
  5. extractionextracted with ethyl acetate (2×25 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customto give an orange oil
  10. customThe crude product was purified by chromatography on silica eluting with EtOAc/iso-hexane
  11. customfollowed by further purification by chromatography on silica eluting with DCM/MeOH

Sources & evidence

ORD record
ord-6537d41ce90748c6965190bdd6f0e3bc
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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