HCID 19899051, compound → HCID 19899026, compound

HRID 1196678Notes

Reaction equation

HRID 1196678 reaction equation
[CH3:1][O:2][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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][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:7][CH:8]=1

Participants

5

Reactant 1

HCID 19899051HCID 19899051, compound

Product 1

HCID 19899026HCID 19899026, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

2.32 g (0.006 mol) of methyl 3a,5,6,7,8,8a-hexahydro-3-(4-methoxyphenyl)-8a-pyrrolidino-4H-cyclohept[d]isoxazole-7-carboxylate were dissolved in a mixture of 6 ml of glacial acetic acid, 6 ml of water and 6 ml of concentrated sulfuric acid. The mixture was held at 100° C. for 1 hour, cooled and diluted with 20 ml of water to give a white precipitate which was filtered off, washed and dried. Crystallization from ethyl acetate gave 1.04 g of 5,6,7,8-tetrahydro-3-(4-methoxyphenyl)-4H-cyclohept[d]isoxazole-7-carboxylic acid of melting point 194°-196° C.

Workup

  1. temperaturecooled
  2. customto give a white precipitate which
  3. filtrationwas filtered off
  4. washwashed
  5. customdried
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b7259c556fa14aefb63afe638eef6cf4
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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