Ozone → HCID 11358871, compound

HRID 2229341Notes

Reaction equation

HRID 2229341 reaction equation
[O:1]=[O+][O-].[CH3:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH3:26])[C:10](=[O:25])[C:11]3[CH:21]=[C:20]([CH2:22][CH:23]=C)[CH:19]=[N:18][C:12]=3[N:13]([CH2:16][CH3:17])[C:14]=2[N:15]=1.[BH4-].[Na+].[NH4+].[Cl-]>C(Cl)Cl.CO>[CH3:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH3:26])[C:10](=[O:25])[C:11]3[CH:21]=[C:20]([CH2:22][CH2:23][OH:1])[CH:19]=[N:18][C:12]=3[N:13]([CH2:16][CH3:17])[C:14]=2[N:15]=1

Participants

7

Reactant 4

HCID 24823OzoneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 18466629HCID 18466629, compound

Product 1

HCID 11358871HCID 11358871, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stream of O3 was introduced into a cold (−78° C.) solution of 5,11-dihydro-2,5-dimethyl-11-ethyl-8-(2-propenyl)-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (187 mg, 0.6 mmol) and Sudan III in CH2Cl2 (3 mL) and MeOH (3 mL). When the pink solution turned brown, O2 was bubbled through the solution for 10 min. NaBH4 (57 mg, 1.52 mmol) was then added and the solution was allowed to warm to room temperature. After 30 min, an additional amount of NaBH4 (20 mg) was added. After 2 h, aqueous saturated NH4Cl was then added and the mixture stirred for 20 min. The solution was concentrated if under reduced pressure and extracted with CH2Cl2 (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane 6:4) to give the title compound (111 mg, 58% yield) as a white solid.

Workup

  1. customO2 was bubbled through the solution for 10 min
  2. waitAfter 2 h
  3. concentrationThe solution was concentrated if under reduced pressure
  4. extractionextracted with CH2Cl2 (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (EtOAc:Hexane 6:4)

Sources & evidence

ORD record
ord-8dfe1e0110e7460685b073b6a0031b72
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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