Cesium fluoride → HCID 10535250, compound

HRID 1066020Notes

Reaction equation

HRID 1066020 reaction equation
[CH2:1]([C@@H:8]1[N:11]([Si](C(C)(C)C)(C)C)[C:10](=[O:19])[C@H:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+]>CO>[CH2:1]([C@@H:8]1[NH:11][C:10](=[O:19])[C@H:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 10803401HCID 10803401, compound

Product 1

HCID 10535250HCID 10535250, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4(S)-benzyl-1-(tert-butyldimethyl-silyl)-3(S)-methylazetidin-2-one (557 mg, 1.92 mmol) in MeOH (25 mL) at 0° was added cesium fluoride (439 mg, 2.89 mmol). After 1 h MeOH was evaporated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with H2O and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 50% EtOAc in hexane) to give 4(S)-benzyl-3(S)-methylazetidin-2-one (239 mg, 71% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ7.35-7.17 (m, 5H), 5.78 (brs, 1H), 3.46 (ddd, J=8.0, 5.9, 2.0 Hz, 1H), 2.98 (dd, J=13.5, 5.9 Hz, 1H), 2.91 (qd, J=7.3, 2.0 Hz, 1H), 2.84 (dd, J=13.5, 8.0 Hz, 1H), 1.26 (d, J=7.3 Hz, 3H).

Workup

  1. customAfter 1 h MeOH was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic phase was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-a3ed87098eb44d1a86bcfafd9faaaef3
Source dataset
uspto-grants-2001_06
Patent number
US06242439B1

Reaction notes

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