Tetrahydrofuran → HCID 12148215, compound

HRID 403503Notes

Reaction equation

HRID 403503 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]([Mg]Br)=[CH2:16].C1COCC1>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH:15]=[CH2:16])([OH:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418507HCID 178418507, compound

Product 1

HCID 12148215HCID 12148215, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (2.5 g, 12.5 mmol) was dissolved in 25 ml of diethylether and cooled to 0° C. A 1M solution of vinylmagnesiumbromide in THF (16.3 ml, 16.31 mmol) was added dropwise at 0° C. After 90 min stirring at 0° C., the reaction mixture was quenched with NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2 SO4 and evaporated. The crude product was further purified by flash chromatography (silicagel, cyclohexane/ethylacetate 4:1).

Workup

  1. customthe reaction mixture was quenched with NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried over Na2 SO4
  5. customevaporated
  6. customThe crude product was further purified by flash chromatography (silicagel, cyclohexane/ethylacetate 4:1)

Sources & evidence

ORD record
ord-46b1e50322bf4762a9dc53acefa69a13
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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