Sodium bis(2-methoxyethoxy)aluminiumhydride → 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine

HRID 1618537Notes

Reaction equation

HRID 1618537 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]2=[N:7][CH:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:10]=[C:5]2[NH:4][C:3]1=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[C:6]2=[N:7][CH:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:10]=[C:5]2[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 672845953,3-dimethyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Product 1

HCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 3,3-dimethyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (425 mg, 1.719 mmol) in toluene (14 mL) at 0° C. was added sodium bis(2-methoxyethoxy)aluminum hydride (3.3 M solution in toluene, 1.56 mL, 5.16 mmol). The reaction was stirred while warming to rt for 4 h. After this time the reaction was carefully quenched with water (5 mL) and then diluted with DCM (50 mL) and treated with saturated aqueous solution Na2S2O3 (20 mL). The separated aqueous layer was then extracted with DCM (20 mL) and the combined organic layers were washed with brine (20 mL) and then dried over MgSO4, filtered and evaporated in vacuo to give 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine. Mass Spectrum (ESI) m/e=234.2 (M+1).

Workup

  1. customAfter this time the reaction was carefully quenched with water (5 mL)
  2. additiondiluted with DCM (50 mL)
  3. additiontreated with saturated aqueous solution Na2S2O3 (20 mL)
  4. extractionThe separated aqueous layer was then extracted with DCM (20 mL)
  5. washthe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-156d1d9ecc0642fdbfbb236e6899f2ba
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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