Sodium triacetoxyborohydride → Ethyl 6-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)hexanoate

HRID 517898Notes

Reaction equation

HRID 517898 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.O=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11171124Ethyl 6-oxohexanoate2×HCID 666645252,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Product 1

HCID 89689920Ethyl 6-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)hexanoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate B) (2.0 g, 6.34 mmol) and ethyl 6-oxohexanoate (Intermediate A) (2.508 g, 12.68 mmol) in 1,2-dichloroethane (50 ml) was treated with sodium triacetoxyborohydride (3.36 g, 15.85 mmol) and the resultant suspension was stirred at room temperature overnight. The solution was treated with sat.NaHCO3 and extracted with DCM (×3). The organic extracts were dried (MgSO4) and evaporated under reduced pressure. The residue was loaded onto an Isolute® SCX-2 cartridge and eluted with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions were concentrated under reduced pressure and further purified by chromatography on silica eluting with 10-50% EtOAc in iso-hexane to afford the titled compound;

Workup

  1. additionThe solution was treated
  2. extractionNaHCO3 and extracted with DCM (×3)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. customevaporated under reduced pressure
  5. washeluted with MeOH
  6. concentrationThe methanolic ammonia fractions were concentrated under reduced pressure
  7. customfurther purified by chromatography on silica eluting with 10-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-260e12903989443985adf15e1d2488c0
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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