Sodium borohydride → HCID 70982434, compound

HRID 625930Notes

Reaction equation

HRID 625930 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:18]4[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:18]4[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14][NH:13]3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70982232HCID 70982232, compound

Product 1

HCID 70982434HCID 70982434, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.51 mmol of 5-(1-(4-chlorophenyl)cyclo-butyl)-7-methoxy-2,3-dihydrobenzo[f][1,4]oxazepine in 5 ml methanol and 0.1 ml water were added 1.00 mmol sodium borohydride and the mixture was stirred at room temperature over night. The mixture was concentrated and the residue was dissolved in methylene chloride and water was added. The phases were separated using a Chromabond® PTS column. The aqueous phase was extracted with methylene chloride (1×). The combined organic phases were dried over Na2SO4, and filtered and concentrated to give 0.18 g of a crude material, which was purified by flash chromatography. To the combined fractions was added a solution of hydrogen chloride in 2-propanol and concentrated. The residue was dissolved in methanol and concentrated (2×). The material was further purified by flash chromatography to yield 14 mg of 5-(1-(4-chlorophenyl)cyclobutyl)-7-methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine hydrochloride as a white solid (HCl-salt, 15%).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. additionwater was added
  4. customThe phases were separated
  5. extractionThe aqueous phase was extracted with methylene chloride (1×)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give 0.18 g of a crude material, which
  10. customwas purified by flash chromatography
  11. additionTo the combined fractions was added a solution of hydrogen chloride in 2-propanol
  12. concentrationconcentrated
  13. dissolutionThe residue was dissolved in methanol
  14. concentrationconcentrated (2×)
  15. customThe material was further purified by flash chromatography

Sources & evidence

ORD record
ord-03fe7251d16a455582f229c59145dd0e
Source dataset
uspto-grants-2016_04
Patent number
US09309200B2

Reaction notes

Loading…