Water → HCID 59361493, compound

HRID 888767Notes

Reaction equation

HRID 888767 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:14](=[O:15])[CH2:13][NH:12]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH2:22]([N:12]1[CH2:13][C:14](=[O:15])[N:11]1[CH:2]1[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]1[CH2:10]3)[CH2:9]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67303639HCID 67303639, compound

Product 1

HCID 59361493HCID 59361493, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, a solution of 2-(adamantan-2-yl)-1,2-diazetidin-3-one (10.2 mg, 0.05 mmol) in N,N-dimethylformamide (1 mL), potassium carbonate (28.0 mg, 0.100 mmol) and benzyl bromide (35.0 mg, 0.100 mmol) were added at room temperature, and the resultant was stirred at the same temperature for 24 hours. The reaction solution was added with water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=2:1), and the title compound (7.60 mg, 48.6%) was obtained as a colorless oil.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe obtained residue was purified

Sources & evidence

ORD record
ord-d800154142be47b992715d6ab4c9a817
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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