Water → 8-Azidomethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol

HRID 656477Notes

Reaction equation

HRID 656477 reaction equation
[O:1]1[CH2:3][C:2]21[CH2:8][CH2:7][CH2:6][N:5]1[CH:9]=[N:10][CH:11]=[C:4]21.[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C)C=O>[N:12]([CH2:3][C:2]1([OH:1])[CH2:8][CH2:7][CH2:6][N:5]2[CH:9]=[N:10][CH:11]=[C:4]12)=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 866299996,7-dihydro-5H-spiro[imidazo[1,5-a]pyridine-8,2'-oxirane]

Product 1

HCID 866299988-Azidomethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5 mmol of 6,7-dihydro-5H-spiro[imidazo[1,5-a]pyridine-8,2′-oxirane] in 15 ml of N,N-dimethylformamide is admixed with 10 mmol of sodium azide and the reaction mixture is heated at 60° C. for 4 hours. The mixture is poured into water and extracted with tert-butyl methyl ether. The combined organic extracts are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.

Workup

  1. extractionextracted with tert-butyl methyl ether
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-ccc038570b394a97a4903bdc27837725
Source dataset
uspto-grants-2011_12
Patent number
US08071773B2

Reaction notes

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