Sodium bis(2-methoxyethoxy)aluminiumhydride → 6'-Bromo-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

HRID 1618522Notes

Reaction equation

HRID 1618522 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=O)[C:8]3([CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:6][CH:7]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH2:9][C:8]3([CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 669543106'-Bromo-1',2'-dihydrospiro[oxane-4,3'-pyrrolo[3,2-b]pyridine]-2'-one

Product 1

HCID 672845606'-Bromo-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure K using 6′-bromo-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridin]-2′(1′H)-one (138 mg, 0.487 mmol) and sodium bis(2-methoxyethoxy)aluminium hydride (304 μL, 1.560 mmol) in toluene (3 mL). After purification 6′-bromo-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] was obtained as a white solid.

Workup

  1. customPrepared
  2. customAfter purification 6′-bromo-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-07d2e44e17754d0dacd89e2043f465e6
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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