Hydrochloric Acid → 2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

HRID 641529Notes

Reaction equation

HRID 641529 reaction equation
Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[CH:12]1([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][C:28]4[N:33]=[C:32]5[C:34](=[O:38])[NH:35][C:36](=[O:37])[C:31]5=[CH:30][CH:29]=4)=[CH:26][C:19]=3[CH2:18][CH2:17]2)[CH2:15][CH2:14][CH2:13]1.[BH4-].[Na+].Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[CH:12]1([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][C:28]4[N:33]=[C:32]5[CH:34]([OH:38])[NH:35][C:36](=[O:37])[C:31]5=[CH:30][CH:29]=4)=[CH:26][C:19]=3[CH2:18][CH2:17]2)[CH2:13][CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24840Magnesium perchlorateHCID 4311764Sodium borohydrideHCID 104738952-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

Product 1

HCID 574402952-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Magnesium perchlorate (0.89 g) was added to a solution of 2-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (E233) (0.72 g, 1.98 mmol) in a mixture of chloroform:methanol (1:1; 20 ml) at 0° C. under argon. Sodium borohydride (113 mg) was added and the mixture stirred at for 0.5 h. The mixture was adjusted to pH 2 with HCl (2M), stirred for an additional 0.5 h, then taken to pH 11 with sodium hydroxide (2N). The mixture was then extracted with dichloromethane and the combined organic extracts dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the title compound (E234); MS (ES+) m/e 366 [M+H]+.

Workup

  1. stirringstirred for an additional 0.5 h
  2. extractionThe mixture was then extracted with dichloromethane
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-75eda5e251b34728b7acb9983573f5db
Source dataset
uspto-grants-2010_04
Patent number
US07696193B2

Reaction notes

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