Oxygen → 11-Ethyl-8-(2-hydroxyethyl)-5-methyl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2212812Notes

Reaction equation

HRID 2212812 reaction equation
[O:1]=O.[CH2:3]([N:5]1[C:11]2[N:12]=[CH:13][C:14]([CH2:16][CH:17]=C)=[CH:15][C:10]=2[C:9](=[O:19])[N:8]([CH3:20])[C:7]2[CH:21]=[CH:22][CH:23]=[N:24][C:6]1=2)[CH3:4].[BH4-].[Na+].[NH4+].[Cl-]>C(Cl)Cl.CO>[CH2:3]([N:5]1[C:11]2[N:12]=[CH:13][C:14]([CH2:16][CH2:17][OH:1])=[CH:15][C:10]=2[C:9](=[O:19])[N:8]([CH3:20])[C:7]2[CH:21]=[CH:22][CH:23]=[N:24][C:6]1=2)[CH3:4]

Participants

7

Reactant 4

HCID 977OxygenHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21955848HCID 21955848, compound

Product 1

HCID 47071711-Ethyl-8-(2-hydroxyethyl)-5-methyl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stream of ozonized oxygen was bubbled through a cold (−78° C.) solution of 5,11-dihydro-11-ethyl-5-methyl-8-(2-propenyl)-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one 1g (22.19 g, 75.4 mmol) in CH2Cl2 (150 mL) and MeOH (150 mL) for 2.5 h. A stream of N2 was next bubbled through the solution for 15 min and then solid NaBH4 (4.99 g, 132 mmol) was added to the solution. The reaction mixture was allowed to warm to room temperature. After 1 h, aqueous saturated NH4Cl (200 mL) was added and the mixture was stirred at room temperature for 2 h. The organic solvents were removed under reduced pressure. Water (300 mL) and CHCl3 (300 mL) were added to the residue. The phases were separated and the aqueous layer was extracted with CHCl3 (3×300 mL). The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc/CHCl3, 4/1) to give compound 1 h (16.1 g, 72% yield) as a white solid.

Workup

  1. customA stream of N2 was next bubbled through the solution for 15 min
  2. customThe organic solvents were removed under reduced pressure
  3. additionWater (300 mL) and CHCl3 (300 mL) were added to the residue
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with CHCl3 (3×300 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (EtOAc/CHCl3, 4/1)
  10. customto give compound 1 h (16.1 g, 72% yield) as a white solid

Sources & evidence

ORD record
ord-c1f8707028ae425c983164877a3b4fb3
Source dataset
uspto-grants-2006_09
Patent number
US07105510B2

Reaction notes

Loading…