Water → HCID 66645871, compound

HRID 1694919Notes

Reaction equation

HRID 1694919 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]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH:16]=2)[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]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH:16]=2)[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 66645728HCID 66645728, compound

Product 1

HCID 66645871HCID 66645871, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.47 ml of a borane-tetrahydrofuran complex (1.2 mol/l) (4.16 mmol) was added to a solution of 456 mg of 4-[3-(3-methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in the above reaction (1.16 mmol) in tetrahydrofuran (4.16 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, 4.16 ml of a 1 N sodium hydroxide aqueous solution (4.16 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 370 mg of the title compound (yield: 82%).

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-6d625942fc634ccb99e815cb0e78ab56
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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