Sodium Hydroxide → 4-N-Boc-2-hydroxymethylpiperazine

HRID 1792006Notes

Reaction equation

HRID 1792006 reaction equation
[OH-].[Na+].C(OC([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]1[CH2:23][OH:24])=O)(C)(C)C>C(O)C>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][NH:10][CH:11]([CH2:23][OH:24])[CH2:12]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22711445Di-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

Product 1

HCID 223865084-N-Boc-2-hydroxymethylpiperazineYield 113.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (5.42 g) was added to a solution of 2-hydroxymethylpiperazine-1,4-dicarboxylic acid di-tert-butyl ester (10.87 g) in ethanol (300 ml), and the reaction mixture was heated to reflux for 16 hours. The solvent was removed by distillation at reduced pressure, and the residue was dissolved in ethyl acetate (400 ml) and water (50 ml). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by distillation at reduced pressure to give 8.46 g of the title compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed by distillation at reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (400 ml)
  5. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation at reduced pressure

Sources & evidence

ORD record
ord-481d891505d2470498fdb98a57d6e16d
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

Loading…