Ethyl Acetate → 2-(4-Chlorophenylamino)-1-cyclopentanemethanol

HRID 359103Notes

Reaction equation

HRID 359103 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[C:20](OCC)=[O:21])=[CH:10][CH:9]=1.C(OCC)(=O)C.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[CH2:20][OH:21])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 15086642HCID 15086642, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 150866432-(4-Chlorophenylamino)-1-cyclopentanemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.60 g) was suspended in THF (70 ml) under ice cooling and thereto a solution of ethyl 2-(4-chlorophenylamino)-1-cyclopentanecarboxylate in THF (about 16 ml) was added gradually, and the mixture was stirred at room temperature for 14 hours. Ethyl acetate and a small amount of 1N aqueous sodium hydroxide solution were added to the reaction mixture to decompose the excess reducing agent. The mixture was filtered and concentrated under reduced pressure to give the oily desired product (3.24 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-832612e110bc4d3bbdc70a649c98c860
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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