Sodium borohydride → 3-Benzyl-1,2,3,4,5,6-hexahydro-7h-pyrido[3,4-d][2]benzazepin-7-one

HRID 1896140Notes

Reaction equation

HRID 1896140 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:19]=[CH:18][C:17]2[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[NH:13][CH2:12][C:11]=2[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C.O>[CH2:2]([N:9]1[CH2:19][CH2:18][C:17]2[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[NH:13][CH2:12][C:11]=2[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 672477733-Benzyl-7-oxo-6,7-dihydro-5h-pyrido[3,4-d][2]benzazepin-3-ium bromide

Product 1

HCID 595485223-Benzyl-1,2,3,4,5,6-hexahydro-7h-pyrido[3,4-d][2]benzazepin-7-one

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a suspension of Example 180E (17.7 g, 46.4 mmol) in 200 mL of ethanol/water (4:1) at 0° C. was added NaBH4 (8.9 g, 0.232 mol) portion-wise. After stirring for 0.5 hour, the mixture was quenched with 1 N HCl to pH 4-5 and concentrated under reduced pressure. The residue was dissolved in 100 mL of saturated aqueous K2CO3 and extracted with dichloromethane. The organic phase was washed with brine, dried and purified by column chromatography on silica gel eluting with dichloromethane/methanol (30:1) to obtain the title compound.

Workup

  1. customthe mixture was quenched with 1 N HCl to pH 4-5
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 100 mL of saturated aqueous K2CO3
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with brine
  6. customdried
  7. custompurified by column chromatography on silica gel eluting with dichloromethane/methanol (30:1)

Sources & evidence

ORD record
ord-abe0057a36854bfda15451d650b60d2a
Source dataset
uspto-grants-2013_08
Patent number
US08518933B2

Reaction notes

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