Benzyl Bromide → HCID 23152775, compound

HRID 1012250Notes

Reaction equation

HRID 1012250 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:36]([O:21][C:19]1[CH:18]=[CH:17][C:15]2[C:16]3[N:10]([CH2:11][CH2:12][O:13][C:14]=2[CH:20]=1)[C:9]1[CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=[CH:25][C:8]=1[C:7]=3[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 11994998Methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate

Product 1

HCID 23152775HCID 23152775, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (150 mg, 0.38 mmol) in N,N-dimethylformamide (2.0 ml) were added potassium carbonate (132 mg, 0.96 mmol) and benzyl bromide (0.07 ml, 0.61 mmol) and the mixture was stirred at 60° C. for 3 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give methyl 3-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (173 mg, yield 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b2bb82e79b5e44a3857abebba74f966c
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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