Sodium Hydroxide → HCID 18695487, compound

HRID 1586450Notes

Reaction equation

HRID 1586450 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:11]1[CH2:16][CH2:15][C:14](=[CH:17][C:18](OCC)=[O:19])[CH2:13][CH2:12]1)[CH2:8][CH2:9][CH3:10].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH2:7]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH2:12]1)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 18695618HCID 18695618, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18695487HCID 18695487, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of lithium aluminum hydride (0.96 g) in THF (90 ml) was ice-cooled, to which was added dropwise a solution of ethyl 1-n-butyl-4-piperidylideneacetate (3.40 g) obtained in Preparation Example 11 in THF (60 ml) over a period of 10 minutes with stirring. The mixture was stirred under ice-cooling for 10 minutes, and then at room temperature for further 2 hours. To the reaction solution were successively added water (4 ml), a 15% aqueous solution of sodium hydroxide (4 ml), water (12 ml), and anhydrous magnesium sulfate, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was filtered off with Celite, and the solvent was distilled off under reduced pressure. To a solution of the residue in ethanol (150 ml) was added platinum (IV) oxide (0.50 g), and the mixture was shaken at room temperature under hydrogen atmosphere at 2 kg/cm2 for 11 hours. The reaction solution was filtered off with Celite, and the solvent was distilled off under reduced pressure to give the title compound (2.76 g) as a yellow oily substance. This compound was used for the subsequent reaction without purification.

Workup

  1. temperaturecooled, to which
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 10 minutes
  4. filtrationThe reaction solution was filtered off with Celite
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo a solution of the residue in ethanol (150 ml) was added platinum (IV) oxide (0.50 g)
  7. stirringthe mixture was shaken at room temperature under hydrogen atmosphere at 2 kg/cm2 for 11 hours
  8. filtrationThe reaction solution was filtered off with Celite
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7b92797e0553479ea30fffacf10ab3a4
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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