Hydrogen Peroxide → HCID 50986395, compound

HRID 2367167Notes

Reaction equation

HRID 2367167 reaction equation
[O:1]=[C:2]1[C@@H:9]2[C@@H:5]([CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]2)[CH2:4][CH2:3]1.OO>O1CCCC1.O>[OH:1][C@H:2]1[C@@H:9]2[C@@H:5]([CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 29948688rel-1,1-Dimethylethyl (3aR,6aS)-hexahydro-4-oxocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 50986395HCID 50986395, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under an inert atmosphere, 1.00 g (4.44 mmol) of tert-butyl (3aR,6aS)-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate is dissolved in 15 mL of anhydrous tetrahydrofuran; the medium is cooled to −78° C. and 6.66 mL (6.66 mmol) of a solution of lithium tri-sec-borohydride (L-Selectride) at 1N in tetrahydrofuran are then added dropwise. The medium is allowed to warm to room temperature over three hours with stirring, and then cooled to 0° C., followed by dropwise addition of 35% aqueous hydrogen peroxide solution until the evolution of gas has ceased. The medium is diluted with water and extracted three times with ethyl acetate. The combined organic phases are washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. 0.826 g (82%) of the expected product is obtained in the form of a colourless oil.

Workup

  1. temperatureto warm to room temperature over three hours
  2. temperaturecooled to 0° C.
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases are washed once with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1e86e5597ea46998776f29612adb73c
Source dataset
uspto-grants-2014_04
Patent number
US08697883B2

Reaction notes

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