Hydrogen Peroxide → HCID 21474131, compound

HRID 2294069Notes

Reaction equation

HRID 2294069 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:10]2([CH2:26][CH:27]=[CH2:28])[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH2:14][CH2:13][C:12]3[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:11]2=3)=[CH:6][CH2:5]1)(=[O:3])[CH3:2].C12BC(CCC1)CCC2.[OH-:38].[Na+].OO>C1COCC1>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:10]2([CH2:26][CH2:27][CH2:28][OH:38])[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH2:14][CH2:13][C:12]3[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:11]2=3)=[CH:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57108136HCID 57108136, compound

Product 1

HCID 21474131HCID 21474131, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 1-acetyl-4-(8-chloro-5, 6-dihydro-11-(2-propenyl)-11H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-yl)-1,2,5,6-tetrahydropyridine(1.0 g, 2.5 mmol) in 50 mL of dry THF, and cooled to 0° C. under a nitrogen atmosphere. Added 9-borabicyclo-[3.3.1]nonane (12.5 mL of 0.5M, 6.25 mmol) via syringe. Warmed slowly room temperature, and stirred for 4 hours. Added 25 weight % NaOH (7.8 mL, 20 mmol) and 30 weight % hydrogen peroxide (4.9 mL, 17.5 mmol), and stirred at room temperature for 16 hours. Added dichloromethane, and washed with saturated NaHSO3, water, and then saturated NaCI. Dried organic solution with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 10% MeOH-EtOAc. Combined appropriate fractions, and evaporated to give 0.16 g (16% yield) of 1-acetyl-4-(8-chloro-5,6-dihydro-11-(3-hydroxypropyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-1,2,5,6-tetrahydropyridine as an oil.

Workup

  1. temperatureWarmed slowly room temperature
  2. stirringstirred at room temperature for 16 hours
  3. washAdded dichloromethane, and washed with saturated NaHSO3, water
  4. filtrationDried organic solution with MgSO4, filtered
  5. customevaporated
  6. customPurified crude product by flash chromatography on silica gel eluting with 10% MeOH-EtOAc
  7. customevaporated

Sources & evidence

ORD record
ord-3f6d6a6a0bfd412a9eaec6bddff97b5e
Source dataset
uspto-grants-1997_11
Patent number
US05688805

Reaction notes

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