Sodium Chloride → HCID 21830998, compound

HRID 1600886Notes

Reaction equation

HRID 1600886 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][CH:11]2[NH:15][C:14](=O)[CH2:13][CH2:12]2)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Na+].[Cl-].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C>[NH:15]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH2:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24436Sodium SulfateHCID 15434756HCID 15434756, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 21830998HCID 21830998, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 313 mg (1.46 mM) of 5-(1H-Pyrrolo[2,3-b]pyridin-3ylmethyl)-pyrrolidin-2-one and 170 mg (4.47 mM) of lithium aluminum hydride was refluxed in 10 mL of dioxane for 5 hours. The solution was cooled to room temperature and the excess lithium aluminum hydride decomposed with 1 mL of saturate NaCl. To this mixture was added 300 mL of ethyl acetate, and 15 g of anhydrous Na2SO4. The reaction mixture was filtered, and evaporated to yield 254 mg of the amine as a dark oil, this material was used directly in the next synthetic step. Mass spectrum: m/e=202(p=1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-ac1e54d35e024f62a8e586fb7b1f68b2
Source dataset
uspto-grants-1999_11
Patent number
US05977131

Reaction notes

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