Water → HCID 18510681, compound

HRID 2219094Notes

Reaction equation

HRID 2219094 reaction equation
[CH3:1][Mg]Cl.[C:4]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([CH:21]2[O:25][N:24]=[C:23]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:22]2)=[O:20])=[CH:14][CH:13]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>C1COCC1>[OH:11][C:4]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([CH:21]2[O:25][N:24]=[C:23]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:22]2)=[O:20])=[CH:16][CH:17]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 9820758HCID 9820758, compoundHCID 178418332HCID 178418332, compound3×

Product 1

HCID 18510681HCID 18510681, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
0 °C

Procedure

) CH3MgCl, 22% (w/w)/THF (0.003 mol) was added dropwise to a cooled (0° C.) solution of (±)-N-(4-benzoylphenyl)-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (0.003 mol) in THF (50 ml). The reaction mixture was stirred for 30 minutes at 0° C. More CH3MgCl, 22% w/w/THF (0.003 mol) was added and the mixture was stirred for 30 minutes at 0° C. Extra CH3MgCl, 22% (w/w)/THF (0.003 mol) was added and the reaction mixture was stirred for 30 minutes at 0° C. The mixture was allowed to warm to RT for 30 minutes, then cooled again to 0° C. Water was added. This mixture was extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The crude oil was crystallized from EtOAc. The precipitate was filtered off, washed with EtOAc, and dried, yielding 0.5 g(50%) of (±)4,5-dihydro-N-[4-(1-hydroxy-1-phenylethyl)phenyl]-3-(3-pyridinyl)-5-isoxazolecarboxamide (compound 51).

Workup

  1. stirringthe mixture was stirred for 30 minutes at 0° C
  2. stirringthe reaction mixture was stirred for 30 minutes at 0° C
  3. temperatureto warm to RT for 30 minutes
  4. temperaturecooled again to 0° C
  5. extractionThis mixture was extracted with CH2Cl2
  6. dry with materialThe separated organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customThe crude oil was crystallized from EtOAc
  10. filtrationThe precipitate was filtered off
  11. washwashed with EtOAc
  12. customdried

Sources & evidence

ORD record
ord-9d874e7096ea41a18ed4ac8db985fe81
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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