Aluminium lithium hydride → HCID 90408900, compound

HRID 2177571Notes

Reaction equation

HRID 2177571 reaction equation
[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH:11]([C:16](OCC)=[O:17])[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH:11]([CH2:16][OH:17])[C:10]=3[N:9]=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90408600HCID 90408600, compound

Product 1

HCID 90408900HCID 90408900, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-4-carboxylate (0.10 g, 0.37 mmol) in THF (10 mL) at −78° C. was added LiAlH4 (1M in THF) (1.1 mL, 1.10 mmol). After 14 h the reaction was quenched with 1 N NaOH, Rochelle's salt, and extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.06 g, 71%). MS (ESI): mass calculated for C13H15N3O, 229.12. m/z found 230.1 [M+H]+.

Workup

  1. customAfter 14 h the reaction was quenched with 1 N NaOH, Rochelle's salt
  2. extractionextracted with DCM (3×25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8dde78b79634dad8fb0438d5e324207
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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