HCID 19899041, compound → HCID 19898995, compound

HRID 1196660Notes

Reaction equation

HRID 1196660 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]3[CH2:13][CH2:14][CH:15]([C:17]([O:19]CC)=[O:18])[CH2:16][C:11]3(N3CCCC3)[O:10][N:9]=2)=[CH:4][CH:3]=1>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH:15]([C:17]([OH:19])=[O:18])[CH2:16][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 19899041HCID 19899041, compound

Product 1

HCID 19898995HCID 19898995, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 0.59 g of ethyl 3-(4-chlorophenyl)-3a,4,5,6,7,7a-hexahydro-7a -pyrrolidino-1,2-benzisoxazole-6-carboxylate (mixture of two diastereoisomers) in 25 ml of 2N hydrochloric acid was heated under reflux for 4 hours. After 1 hour, 0.332 g of a crystalline acid separated out. Crystallization from ethyl acetate/toluene gave 0.23 g of 3-(4-chlorophenyl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid of melting point 227°-228° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. custom0.332 g of a crystalline acid separated out
  3. customCrystallization from ethyl acetate/toluene

Sources & evidence

ORD record
ord-73dffb8a582b48ac81492a2df0e3e6b5
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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