Sodium sulfate decahydrate → HCID 66803090, compound

HRID 1528287Notes

Reaction equation

HRID 1528287 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:18])[C:13](=O)[NH:12][C@H:11]2[CH2:15][CH2:16][CH2:17][C@H:10]2[NH:9]1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[H][H]>O1CCOCC1>[CH3:7][C:8]1([CH3:18])[NH:9][C@H:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[NH:12][CH2:13]1

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 66800490HCID 66800490, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66803090HCID 66803090, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Lithium aluminum hydride (541 mg, 14.3 mmol) was added to an anhydrous dioxane (40 mL) solution of cis-3,3-dimethyloctahydrocyclopentapyrazin-2-one (2.00 g, 11.9 mmol) with stirring at room temperature, and the mixture was gradually heated and stirred for 10 minutes under reflux. The reaction mixture was cooled to ice temperature. Then, sodium sulfate decahydrate was added thereto in small portions until no hydrogen gas was generated. Then, the mixture was stirred at room temperature for 1 hour. Insoluble matter was filtered through celite, and the filtrate was concentrated. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/hexane= 1/10) to obtain cis-2,2-dimethyloctahydro-1H-cyclopenta[b]pyrazine (1.67 g, 91%) in a pale yellow oil form.

Workup

  1. temperaturethe mixture was gradually heated
  2. stirringstirred for 10 minutes
  3. temperatureunder reflux
  4. temperatureThe reaction mixture was cooled to ice temperature
  5. stirringThen, the mixture was stirred at room temperature for 1 hour
  6. filtrationInsoluble matter was filtered through celite
  7. concentrationthe filtrate was concentrated
  8. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/hexane= 1/10)

Sources & evidence

ORD record
ord-079feefae1ca45a39f275a4da698897c
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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