Ethyl Acetate → HCID 69079433, compound

HRID 1916651Notes

Reaction equation

HRID 1916651 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[I:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=O)[CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1.CCOC(C)=O.[OH-].[Na+]>C1COCC1.O>[I:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2824673HCID 2824673, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 69079433HCID 69079433, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2.25 mL (2.25 mmol) 1 M lithium aluminium hydride solution are added to a solution of 500 mg (1.51 mmol) N-(4-iodo-phenyl)-2-pyrrolidin-1-yl-acetamide in 10 mL THF at 0° C. and the reaction is stirred for 20 min at this temperature. EtOAc is added and then 85 μL water, 85 μL 15% NaOH solution and finally 256 μL water are added. The precipitate is removed by suction filtering and the filtrate is diluted with 50 mL EtOAc. The organic phase is washed with 30 mL saturated NaHCO3 solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

Workup

  1. customThe precipitate is removed by suction
  2. filtrationfiltering
  3. additionthe filtrate is diluted with 50 mL EtOAc
  4. washThe organic phase is washed with 30 mL saturated NaHCO3 solution
  5. dry with materialThe organic phase is dried over MgSO4

Sources & evidence

ORD record
ord-49c863b0324e4a57915d3cba7fbd0ecc
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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