Benzaldehyde → HCID 46184112, compound

HRID 882710Notes

Reaction equation

HRID 882710 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH2:11])[CH2:8]2.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[C:21]([CH3:28])([CH3:27])[C:22](OCC)=[O:23].Cl>C(O)C.[Zn]>[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[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:21]([CH3:28])([CH3:27])[C:22]1=[O:23])[CH2:8]2

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 253322-Aminoadamantane

Product 1

HCID 46184112HCID 46184112, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-adamantylamine (50.0 mg, 0.330 mmol) in ethanol (2 mL) was added with benzaldehyde (56.3 mg, 0.330 mmol) at room temperature, and the resultant was stirred at the same temperature for 1.5 hours. The reaction solution was concentrated in vacuo. The obtained residue was dissolved in toluene (5 mL), and sequentially added with ethyl 2-bromoisobutyrate (109 mg, 0.660 mmol) and zinc (432 mg, 6.60 mmol) at room temperature. The reaction solution was stirred at 130° C. for 5 hours, and added with hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using preparative thin-layer chromatography (hexane:ethyl acetate=3:1), and 1-(adamantan-2-yl)-3,3-dimethyl-4-phenylazetidin-2-one (65.4 mg, 64.0%) was obtained as a white crystalline powder.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. dissolutionThe obtained residue was dissolved in toluene (5 mL)
  3. stirringThe reaction solution was stirred at 130° C. for 5 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-697c2977aeb04bf8b9cec086140eedc9
Source dataset
uspto-grants-2012_08
Patent number
US08236789B2

Reaction notes

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