Methanol → HCID 23121838, compound

HRID 1713544Notes

Reaction equation

HRID 1713544 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)(C)C.[BH4-].[Na+].C(OCC)(=O)C.[H-].[Na+].[CH3:39][OH:40]>>[O:40]=[C:39]1[N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]2[CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:28]1

Participants

6

Reactant 5

HCID 887MethanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 69645502HCID 69645502, compound

Product 1

HCID 23121838HCID 23121838, compoundYield 57%

Procedure

Bis(1,1-dimethylethyl)2-benzoyl-1,4-piperazinedicarboxylate (0.10 g, 0.26 mmol) was dissolved in methanol (2 mL), sodium borohydride (19 mg, 0.51 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (3 mL), 60% sodium hydride (12 mg, 0.30 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was extracted with ethyl acetate, washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to obtain the title compound (47 mg, yield 57%) as a diastereomer mixture. Diastereomer ratio (α:β=1:5).

Workup

  1. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in N,N-dimethylformamide (3 mL)
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. extractionThe resulting mixture was extracted with ethyl acetate
  7. washwashed with a 0.5 M aqueous sodium hydrogen carbonate solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-58a6bcffd39841ebb5144f82701f2228
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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