Potassium Hydroxide → 2-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazine

HRID 1714804Notes

Reaction equation

HRID 1714804 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[C:16](=O)[NH:15][CH2:14][CH2:13][N:12]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+]>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][NH:15][CH2:14][CH2:13][N:12]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 231559092-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine

Product 1

HCID 231556182-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazineYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolving 2.00 g of 2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine as synthesized in the above step in 50 ml of tetrahydrofuran, 1.00 g of lithium aluminium hydride was added to the solution which then was heated under reflux for 16 hours. To the solution 10% aqueous potassium hydroxide solution was added, the insoluble matter was filtered off, extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (methanol:chloroform=1:19) to provide 1.27 g (66%) of 2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonylpiperazine.

Workup

  1. temperaturethen was heated
  2. temperatureunder reflux for 16 hours
  3. filtrationthe insoluble matter was filtered off
  4. extractionextracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified on silica gel column chromatography (methanol:chloroform=1:19)

Sources & evidence

ORD record
ord-30d5f4a6f16e45f4873d184662d36bc2
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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