Cesium fluoride → HCID 86701372, compound

HRID 515596Notes

Reaction equation

HRID 515596 reaction equation
[F-].[Cs+].[CH2:3]([O:10][N:11]1[C:17](=[O:18])[N:16]2[CH2:19][C@H:12]1[CH2:13][CH2:14][C@H:15]2[C:20]1[CH:24]=[C:23]([Si](C)(C)C)[O:22][N:21]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CC#N.CCO>[CH2:3]([O:10][N:11]1[C:17](=[O:18])[N:16]2[CH2:19][C@H:12]1[CH2:13][CH2:14][C@H:15]2[C:20]1[CH:24]=[CH:23][O:22][N:21]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86701371HCID 86701371, compound

Product 1

HCID 86701372HCID 86701372, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21984225Acetonitrile ethanolSolvent

Procedure

CsF (230 mg, 1.512 mmol was added to a solution of (2S,5R)-6-(benzyloxy)-2-(5-(trimethylsilyl)isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (187 mg, 0.504 mmol) in CH3CN/EtOH (15 mL, 3:1). After stirring at rt for 2 hrs, the reaction mixture was concentrated and the residue was dissolved in DCM (25 mL), washed with water (3×), and saturated sodium chloride, then, dried, and concentrated. The residue was purified by silica gel column chromatography (6:1 petroleum ether/EA) to afford (2S,5R)-6-(benzyloxy)-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (116 mg, 77%) as a white solid. ESI-MS (EI+, m/z): 300 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in DCM (25 mL)
  3. washwashed with water (3×), and saturated sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (6:1 petroleum ether/EA)

Sources & evidence

ORD record
ord-1888b2c150fa4966970cf63ec241f1bb
Source dataset
uspto-grants-2015_08
Patent number
US09108966B2

Reaction notes

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