Water → HCID 118598891, compound

HRID 1050423Notes

Reaction equation

HRID 1050423 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8](=[O:25])[N:9]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:3]=12.[H-].[Na+].I[CH3:29].O>O1CCCC1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:9]2[C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:3]3[C:2](=[O:1])[CH:7]=[CH:6][N:5]([CH3:29])[C:4]=3[C:8]2=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178490843HCID 178490843, compound

Product 1

HCID 118598891HCID 118598891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-hydroxy-6′-(4-methoxybenzyl)spiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridin]-7′(6′H)-one (1.0 mmol, 1 eq) in tetrahydrofuran (25 mL), add sodium hydride (2.5 mmol, 2.5 eq) at 0° C. and stir for 20 min. Add iodomethane (2.5 mmol, 2.5 eq) to the above mixture and stir for 16 h. After completion add water to the reaction and extract with ethyl acetate. Remove the solvent under reduced pressure to get the crude which is purified by column chromatography to give 6′-(4-methoxybenzyl)-1′-methylspiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridine]-4′,7′(1′H,6′H)-dione (6).

Workup

  1. customto the reaction
  2. extractionextract with ethyl acetate
  3. customRemove the solvent under reduced pressure
  4. customto get the crude which
  5. customis purified by column chromatography

Sources & evidence

ORD record
ord-567487a2f3c340cca276a02086b73d39
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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