Water → HCID 66658602, compound

HRID 2074861Notes

Reaction equation

HRID 2074861 reaction equation
C[O:2][C:3]([C@@H:5]1[NH:10][C:9](=O)[CH2:8][N:7]2[CH2:12][CH2:13][CH2:14][C@@H:6]12)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C@@H:5]1([CH2:3][OH:2])[NH:10][CH2:9][CH2:8][N:7]2[CH2:12][CH2:13][CH2:14][C@@H:6]12

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15870278HCID 15870278, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 66658602HCID 66658602, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cis-methyl-3-oxooctahydropyrrolo[1,2-a]pyrazine-1-carboxylate (Prepared according literature procedure: Heterocycles, 52(3), 2000)(270 mg) in anhydrous THF (10 mL) under a Nitrogen atmosphere at 0° C., lithium aluminium hydride (1M in THF, 6.8 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 1 hour, then allowed to reach rt and stirred at this temperature for 30 minutes. Water (260 microL), NaOH (1M solution, 260 microL) and water (780 microL) were then added to the solution and the formation of a white precipitate was observed. The suspension was filtered over a Gooch funnel. The organic filtrate was dried and concentrated in vacuo to give the desired compound (198 mg) as yellow oil.

Workup

  1. customto reach rt
  2. stirringstirred at this temperature for 30 minutes
  3. filtrationThe suspension was filtered over a Gooch funnel
  4. customThe organic filtrate was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3851691fdd654434a774d8367a44e51f
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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