Potassium Carbonate → HCID 17943141, compound

HRID 1452218Notes

Reaction equation

HRID 1452218 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][CH: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 17943141HCID 17943141, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Racemic 3-hydroxybutyl rosylate was prepared in a manner described by Ferreira et al., Tetrahedron, 46, pp. 6311-6318, (1990). To a solution of the racemic tosylate (9.2 g, 37.7 mmol) in acetonitrile (190 ml) was added 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (8.3 g, 37.7 mmol) followed by milled potassium carbonate (7.8 g, 56.6 mmol) at room temperature under nitrogen. The reaction mixture was warmed to reflux for 4.5 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 preparative HPLC (silica gel, 10% MeOH/EtOAc) afforded 6.3 g (57%), m.p.=100°-102° C.

Workup

  1. customRacemic 3-hydroxybutyl rosylate was prepared in a manner
  2. temperatureThe reaction mixture was warmed
  3. temperatureto reflux for 4.5 hours
  4. customThe solids were removed via filtration through a pad of Celite
  5. washwere washed with EtOAc
  6. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-85db9953b04e4aebbaadbfba9566a0f6
Source dataset
uspto-grants-1997_02
Patent number
US05605913

Reaction notes

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