HCID 19899112, compound → HCID 67895933, compound

HRID 1196683Notes

Reaction equation

HRID 1196683 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13](=[CH2:22])[CH2:14][CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:17][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[C@H:13]([CH3:22])[CH2:14][CH2:15][C@H:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:17][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[C@H:13]([CH3:22])[CH2:14][CH2:15][C@@H:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:17][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 19899112HCID 19899112, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 67895933HCID 67895933, compoundHCID 67896312HCID 67896312, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

1 g (3.13 mmol) of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylene-4H-cyclohept[d]isoxazole-7-carboxylate was dissolved in 60 ml of glacial acetic acid and 0.3 g of 5% platinum-on-carbon catalyst was added under a nitrogen atmosphere. The mixture was shaken in a hydrogen atmosphere at room temperature and under atmospheric pressure for 8 hours. The catalyst was removed by filtration and washed with glacial acetic acid. The filtrate was evaporated and the residue was chromatographed on silica gel using 20% ethyl acetate in hexane for the elution. There were obtained 0.47 g of methyl cis-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methyl-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 90°-91° C. and 0.45 g of methyl trans-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methyl-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 108° C.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with glacial acetic acid
  3. customThe filtrate was evaporated
  4. customthe residue was chromatographed on silica gel using 20% ethyl acetate in hexane for the elution

Sources & evidence

ORD record
ord-55f42909c9b9477bb21be964aa23015b
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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