Water → HCID 23121914, compound

HRID 1713524Notes

Reaction equation

HRID 1713524 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[C:4](=[O:11])[O:3]1.C(N(CC)CC)C.[C:20](Cl)(=[O:28])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>O1CCCC1>[CH3:1][C:2]1([CH3:12])[CH:6]2[CH2:7][N:8]([C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:28])[CH2:9][CH2:10][N:5]2[C:4](=[O:11])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 231220551,1-Dimethylhexahydro-3H-[1,3]oxazolo[3,4-a]pyrazin-3-one

Product 1

HCID 23121914HCID 23121914, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexahydro-1,1-dimethyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.10 g, 0.59 mmol) was dissolved in tetrahydrofuran (10 mL). Triethylamine (0.17 mL, 1.2 mmol) and phenyl chlorocarbonate (0.11 mL, 0.88 mmol) were added, and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:2). After purification, the crystals, which were precipitated while concentrating under reduced pressure, were collected by filtration to obtain the title compound (0.14 g, yield 80%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:2)
  6. customAfter purification
  7. customthe crystals, which were precipitated
  8. concentrationwhile concentrating under reduced pressure
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-17bceb8bfa4442ada05a9a38b1562bca
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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