Aluminium lithium hydride → HCID 59569952, compound

HRID 1784933Notes

Reaction equation

HRID 1784933 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:12]([O:11][C:9]1[CH:10]=[C:5]([CH2:4][NH2:1])[CH:6]=[N:7][CH:8]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86612599HCID 86612599, compound

Product 1

HCID 59569952HCID 59569952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 181 mg of 3-(azidomethyl)-5-(benzyloxy)pyridine in 6 mL of THF at 0° C. was added 80.6 mg (2.12 mmol) of LiAlH4. The ice bath was removed and stirring was continued with warming to r.t. After 30 min. the reaction was quenched by adding successively 160 μL of H2O, 160 μL of 15% aqueous NaOH, and 480 μL of brine. The mixture was filtered through Celite and concentrated to yield crude (5-(benzyloxy)pyridin-3-yl)methanamine. The crude product was used without further purification.

Workup

  1. customThe ice bath was removed
  2. customAfter 30 min. the reaction was quenched
  3. additionby adding successively 160 μL of H2O, 160 μL of 15% aqueous NaOH, and 480 μL of brine
  4. filtrationThe mixture was filtered through Celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e2dd2ec31054b9b81d7ac2d16cb3e32
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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