HCID 67895936, compound → HCID 19899064, compound

HRID 1196677Notes

Reaction equation

HRID 1196677 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]3[CH2:14][CH2:15][CH2:16][CH:17]([C:19]([O:21]C)=[O:20])[CH2:18][C:12]3(N3CCCC3)[O:11][N:10]=2)=[CH:5][CH:4]=1>C(O)(=O)C.O.S(=O)(=O)(O)O>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH2:14][CH2:15][CH2:16][CH:17]([C:19]([OH:21])=[O:20])[CH2:18][C:12]=3[O:11][N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 67895936HCID 67895936, compound

Product 1

HCID 19899064HCID 19899064, compoundYield 11.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

3.38 g of methyl 3-(4-trifluoromethylphenyl)-3a,5,6,7,8,8a-hexahydro-8a-pyrrolidino-4H-cyclohept[d]isoxazole-7-carboxylate were dissolved in a mixture of 10 ml of glacial acetic acid, 10 ml of water and 10 ml of concentrated sulfuric acid and heated at 120° C. for 2 hours. The mixture was cooled, diluted with water and extracted three times with 100 ml of methylene chloride each time. The extracts were dried over magnesium sulfate and evaporated and the residue was crystallized from methanol to give 0.32 g of 3-(4-trifluoromethylphenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-7-carboxylic acid of melting point 222°-225° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted three times with 100 ml of methylene chloride each time
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customevaporated
  5. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-747f50c107ed464888d42ac725ac45c2
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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