Potassium Carbonate → HCID 22091894, compound

HRID 1081078Notes

Reaction equation

HRID 1081078 reaction equation
S([C:5]1C=C[C:8](C)=[CH:7][CH:6]=1)([O-])(=O)=O.[F:12][C:13]1[CH:27]=[CH:26][C:16]2[C:17]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[N:18][O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-:29].[K+].[K+]>C(#N)C>[F:12][C:13]1[CH:27]=[CH:26][C:16]2[C:17]([CH:20]3[CH2:21][CH2:22][N:23]([CH2:5][CH2:6][C@@H:7]([OH:29])[CH3:8])[CH2:24][CH2:25]3)=[N:18][O:19][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 85570p-ToluenesulfonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 22091894HCID 22091894, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-Hydroxybutyl rosylate was prepared in a manner described by Ferreira et al., Tetrahedron, 46, pp. 6311-6318, (1990). To a solution of the tosylate (6.8 g, 28.0 mmol) in acetonitrile (150 ml) was added 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (6.2 g, 28.0 mmol) followed by milled potassium carbonate (5.8 g, 42.0 mmol) at room temperature under nitrogen. The reaction mixture was warmed to reflux for 3 hours and allowed to cool to room temperature. The solids were removed via filtration through a pad of Celite and were washed with EtOAc. The combined filtrates were concentrated to give the crude product. Purification via flash column chromatography (silica gel, 0-10% MeOH/EtOAc) afforded 5.5 g (67%) of the desired product as an oil which solidified on standing, m.p.=84°-86° C.

Workup

  1. custom(S)-Hydroxybutyl rosylate was prepared in a manner
  2. temperatureThe reaction mixture was warmed
  3. temperatureto reflux for 3 hours
  4. customThe solids were removed via filtration through a pad of Celite
  5. washwere washed with EtOAc
  6. concentrationThe combined filtrates were concentrated
  7. customto give the crude product
  8. customPurification via flash column chromatography (silica gel, 0-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-1f965cde37774f4ca02690d74df2fdec
Source dataset
uspto-grants-1996_12
Patent number
US05583145

Reaction notes

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