Potassium sodium tartarate → HCID 22005358, compound

HRID 36917Notes

Reaction equation

HRID 36917 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([O:22][CH3:23])[C:9]=2[C:24](OC)=[O:25])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([O:22][CH3:23])[C:9]=2[CH2:24][OH:25])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 537701363-Methyl 5-ethyl 4-(4-fluorophenyl)-6-isopropyl-2-methoxy-pyridine-3,5-dicarboxylate

Product 1

HCID 22005358HCID 22005358, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.48 g (3.95 mmol) of the compound from Example 5 are dissolved in 30 ml of toluene, the solution is cooled to -78° C. under nitrogen and 6.6 ml (10 mmol) of a 1.5 molar solution of diisobutylaluminium hydride in toluene are added dropwise at this temperature. The cooling bath is removed and the mixture is stirred at room temperature for 2 h. After hydrolysis using 20% strength aqueous potassium sodium tartrate solution, the organic phase is separated off, the aqueous phase is washed three times with toluene, and the combined organic phases are washed with saturated sodium chloride solution and dried using sodium sulphate.

Workup

  1. customThe cooling bath is removed
  2. customAfter hydrolysis
  3. customthe organic phase is separated off
  4. washthe aqueous phase is washed three times with toluene
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. customdried

Sources & evidence

ORD record
ord-0cdd43d2293f4b07afd31b99a9d6e306
Source dataset
uspto-grants-1995_05
Patent number
US05418243

Reaction notes

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