Water → 7-Ethenyl-4-azaspiro[2.4]heptan-5-one

HRID 595259Notes

Reaction equation

HRID 595259 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]([CH:7]([CH:14]=[CH2:15])[CH2:8][C:9]([O:11]CC)=O)#[N:6].O>C(OCC)C>[CH:14]([CH:7]1[C:5]2([CH2:2][CH2:1]2)[NH:6][C:9](=[O:11])[CH2:8]1)=[CH2:15]

Participants

5

Reactant 3

HCID 962WaterHCID 91618466Ethyl 3-cyanopent-4-enoateHCID 178418443HCID 178418443, compound

Product 1

HCID 916184657-Ethenyl-4-azaspiro[2.4]heptan-5-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl magnesium bromide (3.0 M in ether, 2.2 mL, 6.6 mmol) was added dropwise over a period of 1 hour to a solution of ethyl 3-cyanopent-4-enoate (500 mg, 3.27 mmol) and Ti(Oi-Pr)4 (1.1 mL, 3.6 mmol) in diethylether (16.4 mL) at room temperature. The reaction mixture was diluted by the dropwise addition of water (3.27 mL) and stirred at room temperature for an additional 30 minutes. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (1:1 ethyl acetate/petroleum ether, Rf=0.3) to afford 7-ethenyl-4-azaspiro[2.4]heptan-5-one as a white solid. MS ESI calc'd. for C8H12NO [M+H]+ 138. found 138. 1H NMR (400 MHz, CDCl3) δ 6.09 (br s, 1H), 5.68-5.60 (m, 1H), 5.08-5.00 (m, 2H), 3.01-2.96 (m, 1H), 2.70-2.64 (m, 1H), 2.40-2.36 (m, 1H), 0.83-0.75 (m, 2H), 0.65-0.58 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto afford the crude product residue
  4. customThe crude product residue was purified by silica gel chromatography (1:1 ethyl acetate/petroleum ether, Rf=0.3)

Sources & evidence

ORD record
ord-9d4fb69bc84545ac9757dae62795ce98
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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