HCID 21931792, compound → HCID 21931744, compound

HRID 1244083Notes

Reaction equation

HRID 1244083 reaction equation
[CH3:1][O:2][C:3]1([O:16][CH3:17])[CH2:8][CH2:7][C:6](=O)[NH:5][CH:4]1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>C1COCC1>[CH3:17][O:16][C:3]1([O:2][CH3:1])[CH2:8][CH2:7][CH2:6][NH:5][CH:4]1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 21931792HCID 21931792, compound

Product 1

HCID 21931744HCID 21931744, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3,3-Dimethoxy-2,3,4,5-tetrahydro-1H-[2,3′]bipyridinyl-6-one (1.0 g, 421 mmol) in 3 mL THF was added borane-dimethylsulfide complex (3.0 mL, 6.0 mmol of a 2 M solution in THF) at 0° C. The solution was stirred at rt overnight, and was then quenched with methanol and heated at reflux for 2 h. The methanol was removed under vacuum and the residue was partitioned between water and chloroform. The mixture was acidified to pH=3 and washed with CHCl3 (3–10 mL). The aqueous material was then basifed to pH=8 with solid NaHCO3 and then was extracted with CHCl3 (3×15 mL). The extracts were dried over MgSO4 and concentrated to give 812 mg (86%) of a pale yellow oil: mass spectrum m/e=223.

Workup

  1. customwas then quenched with methanol
  2. temperatureheated
  3. temperatureat reflux for 2 h
  4. customThe methanol was removed under vacuum
  5. customthe residue was partitioned between water and chloroform
  6. washwashed with CHCl3 (3–10 mL)
  7. extractionwas extracted with CHCl3 (3×15 mL)
  8. dry with materialThe extracts were dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e27ab9ffac1d44dc89e735e874c0af35
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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