Sodium borohydride → HCID 19970847, compound

HRID 975170Notes

Reaction equation

HRID 975170 reaction equation
C([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C:10]2[CH:19]=[C:20]([CH:23]=[O:24])[CH:21]=[CH:22][C:9]1=2)C1C=CC=CC=1.[BH4-].[Na+]>C(O)C>[OH:24][CH2:23][C:20]1[CH:21]=[CH:22][C:9]2[NH:8][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]=2[CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15442751HCID 15442751, compound

Product 1

HCID 19970847HCID 19970847, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzyl-2-formyl-10,11-dihydro-5H-dibenz[b,f]azepine (3.29 g) was dissolved in 200 m. of ethanol, and 0.5 g of sodium borohydride was added to the solution, followed by stirring at room temperature for 30 minutes. The solvent was distilled off under reduced pressure, and the residue was diluted with dichloromethane. The mixture was washed with 1N aqueous hydrochloric acid and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was dissolved in 300 ml of ethanol. To the solution was added 300 mg of 10% palladium carbon and the mixture was stirred in a stream of hydrogen for 4 days. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (2/1)] to give 1.0 g (42%) of the product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washThe mixture was washed with 1N aqueous hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in 300 ml of ethanol
  7. additionTo the solution was added 300 mg of 10% palladium carbon
  8. stirringthe mixture was stirred in a stream of hydrogen for 4 days
  9. filtrationThe catalyst was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (2/1)]

Sources & evidence

ORD record
ord-575b95363d7849dfbf089ed1a00e5bb0
Source dataset
uspto-grants-1997_03
Patent number
US05607955

Reaction notes

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