3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → HCID 68378947, compound

HRID 403504Notes

Reaction equation

HRID 403504 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[CH:14]=[CH2:15]>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([CH2:15][CH:14]=[CH2:13])([OH:12])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178455850HCID 178455850, compound

Product 1

HCID 68378947HCID 68378947, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-Oxo-azetidine-1-carboxylic acid tert-butyl ester (1.37 g, 8 mmol) was dissolved in Et2O (10 ml) and a 1M solution of allylmagnesiumbromid in Et2O (10.4 ml, 10.4 mmol) was added dropwise at 0° C. Stirring was continued at rt overnight. The reaction mixture was quenched with H2O, extracted twice with EtOAc, the organic layer were washed with brine, combined, dried over Na2 SO4, filtered off and concentrated under reduced pressure to give a orange oil. The crude product was purified by flash chromatography (silica gel, EtOAc/cyclohexane 15-25%) which furnished the product as an yellow oil.

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted twice with EtOAc
  3. washthe organic layer were washed with brine
  4. customdried over Na2 SO4
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure
  7. customto give a orange oil
  8. customThe crude product was purified by flash chromatography (silica gel, EtOAc/cyclohexane 15-25%) which

Sources & evidence

ORD record
ord-13bb9bf31e254e34af46bf6d82ac4859
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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