Aluminium lithium hydride → HCID 46178751, compound

HRID 1869219Notes

Reaction equation

HRID 1869219 reaction equation
[CH:1]1([CH:7]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:8][C:9]([NH:11][CH3:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]1([CH:7]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:8][CH2:9][NH:11][CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 57985932HCID 57985932, compound

Product 1

HCID 46178751HCID 46178751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a RT solution of 3-cyclohexyl-N-methyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionamide (170 mg, 0.95 mmol) in THF (10 mL) was added LAH (1 M in THF, 1.5 mL). The mixture was stirred at RT overnight, and an additional LAH (1 M in THF, 2 mL) was added. The resulting mixture was refluxed for 4 hours and then quenched by addition of freshly ground Na2SO4.10H2O (3 g). After stirring for 1 hour, the solids were filtered off and the filtrate was concentrated and purified via preparative HPLC to give [3-Cyclohexyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-methyl-amine. MS M+H=272.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. customquenched by addition of freshly ground Na2SO4.10H2O (3 g)
  3. stirringAfter stirring for 1 hour
  4. filtrationthe solids were filtered off
  5. concentrationthe filtrate was concentrated
  6. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-6eeaef9f409e4f2db4b737f01f143d9e
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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