Water → 4-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethylpiperazine-1-carboxylic acid t-butyl ester

HRID 1694918Notes

Reaction equation

HRID 1694918 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12](=O)[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:10][C:9]1([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:10][C:9]1([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 666455094-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 666456274-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethylpiperazine-1-carboxylic acid t-butyl esterYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.30 ml of a borane-tetrahydrofuran complex (1.2 mol/l) (2.76 mmol) was added to a solution of 303 mg of 4-[2-(3-methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (10e) (0.77 mmol) in tetrahydrofuran (2.8 ml) under a nitrogen atmosphere and under ice-cooling over five minutes, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was cooled in an ice bath. Then, 2.76 ml of a 1 N sodium hydroxide aqueous solution (2.76 mmol) was slowly added and the mixture was further stirred at room temperature for one hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=30/1-10/1) to obtain 276 mg of the title compound (yield: 91%).

Workup

  1. temperaturecooling over five minutes
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. stirringthe mixture was further stirred at room temperature for one hour
  4. extractionfollowed by extraction with ethyl acetate
  5. washThen, the organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=30/1-10/1)

Sources & evidence

ORD record
ord-22f1a752d48b4a07ad46c953ddfcb5f4
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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