Aluminium lithium hydride → HCID 57985871, compound

HRID 1869213Notes

Reaction equation

HRID 1869213 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[N:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH:5]([N:6]2[C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH2:4][CH2:3][OH:2])[CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57985884HCID 57985884, compound

Product 1

HCID 57985871HCID 57985871, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-pyridin-3-yl-3-pyrrolo[3,2-b]pyridin-1-yl-propionic acid methyl ester (150 mg, 0.53 mmol) in THF (10 mL) was added LAH (1M in THF, 0.53 mL). The reaction mixture was stirred at RT for 2 h, and quenched by addition of freshly ground Na2SO4.10H2O (1 g). The mixture was filtered through a celite pad, and the filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH, 8/2/0.1), affording 3-Pyridin-3-yl-3-pyrrolo[3,2-b]pyridin-1-yl-propan-1-ol (66% yield, 85 mg).

Workup

  1. customquenched by addition of freshly ground Na2SO4.10H2O (1 g)
  2. filtrationThe mixture was filtered through a celite pad
  3. concentrationthe filtrate was concentrated
  4. custompurified via flash chromatography (DCM/MeOH/NH4OH, 8/2/0.1)

Sources & evidence

ORD record
ord-7c519b0618ae4afe9f743eb8fd41622c
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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