Ethyl Acetate → HCID 22116060, compound

HRID 1885627Notes

Reaction equation

HRID 1885627 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[O:30][C:29]2[CH:28]=[CH:27][C:11]([O:12][CH2:13][C:14]([N:16]3[CH2:21][CH2:20][CH:19]([C:22](OCC)=[O:23])[CH2:18][CH2:17]3)=O)=[CH:10][C:9]=2[O:8]1.C(OCC)(=O)C.[OH-].[Na+]>C1COCC1>[CH2:7]1[O:30][C:29]2[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH2:14][N:16]3[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]3)=[CH:10][C:9]=2[O:8]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 6458024HCID 6458024, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22116060HCID 22116060, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.81 g) is suspended in THF (60 ml) under ice-cooling and thereto is added dropwise a solution of ethyl 1-(3,4-methylenedioxyphenoxyacetyl)-piperidine-4-carboxylate (4.00 g) in THF (20 ml). The mixture is stirred at room temperature for 30 minutes, and further stirred under refuxing for 14 hours. To the reaction mixture are added ethyl acetate and a small amount of 1N aqueous sodium hydroxide solution to decompose the excess reducing agent. The mixture is filtered and the filtrate is concentrated under reduced pressure to give the desired product (3.25 g).

Workup

  1. temperaturecooling
  2. stirringfurther stirred
  3. waitunder refuxing for 14 hours
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-18394b3dbae94c50a9093a5f02a0a75a
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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