Water → HCID 178426342, compound

HRID 1831075Notes

Reaction equation

HRID 1831075 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:20](=O)[CH2:19][C:18]([CH3:23])([CH3:22])[CH2:17][C:16]2=O)=[CH:11][CH:10]=1.O.[OH-].[Na+]>C(OCC)C>[CH3:22][C:18]1([CH3:23])[CH2:17][CH2:16][N:15]([C:12]2[CH:13]=[N:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22047806HCID 22047806, compound

Product 1

HCID 178426342HCID 178426342, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere lithium aluminium hydride (1.90 g, 50.0 mmol) was added portionwise to a stirred suspension of 6′-methoxy-4,4-dimethyl-4,5-dihydro-3H-[1,3′]bipyridinyl-2,6-dione (2.85 g, 10.0 mmol) in dry diethyl ether (100 mL). After stirring for 3 hours at room temperature, water (1.90 mL), 15% aqueous sodium hydroxide (1.90 mL) and water (5.70 mL) were added respectively. After stirring for 1 hour at room temperature the salts were removed by filtration and washed three times with diethyl ether. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, dichloromethane followed by ethyl acetate/heptane 25/75) yielding the title compound (1.28 g, 58% yield) as a yellow oil.

Workup

  1. stirringAfter stirring for 1 hour at room temperature the salts
  2. customwere removed by filtration
  3. washwashed three times with diethyl ether
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by flash column chromatography (SiO2, dichloromethane followed by ethyl acetate/heptane 25/75)

Sources & evidence

ORD record
ord-0539b51fe6ea4046b9fb2a0694376191
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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