Sodium potassium tartrate tetrahydrate → HCID 23156194, compound

HRID 1890630Notes

Reaction equation

HRID 1890630 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18](OC)=[O:19])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[CH2:18][OH:19])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700DiisobutylaluminumhydrideHCID 23156147HCID 23156147, compound

Product 1

HCID 23156194HCID 23156194, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Compound 12 (2.64 g, 8.16 mmol) was dissolved in toluene (40 mL), and diisobutylaluminum hydride (1.0 mol/L toluene solution, 24.5 mL) was added to the solution at 0° C. under argon atmosphere, followed by stirring at 0° C. for 1.5 hours. The reaction mixture was added with a saturated aqueous (+)-potassium sodium tartrate tetrahydrate solution to terminate the reaction, and diluted with ethyl acetate, followed by stirring vigorously for 30 minutes. The organic layer was separated from the aqueous layer, and washed with saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:1) to obtain Compound 13 (2.32 g, yield 90%).

Workup

  1. customto terminate
  2. customthe reaction
  3. stirringby stirring vigorously for 30 minutes
  4. customThe organic layer was separated from the aqueous layer
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:1)

Sources & evidence

ORD record
ord-6d54593cf4c74d83822b19bb43322497
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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