Cyclopentadiene → HCID 15479426, compound

HRID 1954074Notes

Reaction equation

HRID 1954074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:20])[CH:18]=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH:21]1[CH2:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+:27]>O>[CH:22]12[CH2:21][CH:25]([CH:24]=[CH:23]1)[CH:18]([C:17](=[O:20])[CH2:16][CH2:15][CH2:14][CH2:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[NH:27]2

Participants

5

Reactant 3

HCID 7612CyclopentadieneHCID 25517Ammonium ChlorideHCID 15479425HCID 15479425, compound

Product 1

HCID 15479426HCID 15479426, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.75 g (2.7 mmol) of 6-(3,4,5-trimethoxyphenyl)-2-keto-hexanal and 0.66 ml (8.0 mmol) of cyclopentadiene in 10 ml of aqueous saturated ammonium chloride was stirred at room temperature for 20 hours. The reaction mixture was diluted with 5 ml of water and extracted with 25 ml of ethyl acetate. The aqueous solution was then adjusted to pH=10 with 1N sodium hydroxide (NaOH) and extracted with ethyl acetate. These ethyl acetate layers were combined, dried (Na2SO4) and evaporated to yield 85 mg of 1-(2-Aza-bicyclo[2.2.1]hept-5-en-3-yl)-5-(3,4,5-trimethoxy-phenyl)-pentan-1-one as a mixture of exo and endo isomers. 1H NMR: (CDCl3) δ 6.40 (s, 2 H), 6.22 (m, 1 H), 5.65 (m, 1 H), 3.8 (s, 6 H), 3,75 (s, 3 H), 3.0-4.2 (m, 2 H), 2.5 (m, 5 H), 1.6 (m, 4 H), 1.4 (m, 1 H), 1.2 (m, 1 H). Mass spectrum: m/e=346.2 (p+1).

Workup

  1. extractionextracted with 25 ml of ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a85714eca9ed4e9f8144045e0e1f18bb
Source dataset
uspto-grants-2000_09
Patent number
US06121280

Reaction notes

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