Hydrochloric Acid → cis-7-Chloro-1,2,2a,3,4,9-hexahydro-8-methyl-9bH-cyclobuta[a]carbazole-9b-acetic Acid

HRID 2231724Notes

Reaction equation

HRID 2231724 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][C@:6]12[CH2:22][CH2:21][C@H:7]1[CH2:8][CH2:9][C:10]1[C:11]3[C:16]([NH:17][C:18]=12)=[C:15]([CH3:19])[C:14]([Cl:20])=[CH:13][CH:12]=3)C.Cl>CCO.[OH-].[Na+]>[Cl:20][C:14]1[C:15]([CH3:19])=[C:16]2[C:11]([C:10]3[CH2:9][CH2:8][C@@H:7]4[CH2:21][CH2:22][C@:6]4([CH2:5][C:4]([OH:23])=[O:3])[C:18]=3[NH:17]2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86742522cis-7-chloro-1,2,2a,3,4,9-hexahydro-8-methyl-9bH-cyclobuta[a]carbazole-9b-acetic acid ethyl ester

Product 1

HCID 14302230cis-7-Chloro-1,2,2a,3,4,9-hexahydro-8-methyl-9bH-cyclobuta[a]carbazole-9b-acetic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The ester was dissolved in 22 mL of EtOH and 7 mL of 2.5N NaOH. The solution was refluxed for 30 minutes under nitrogen. The reaction mixture was then acidified with 1N HCl and extracted with 4×50 mL of ethyl acetate. The organic phase was dried over MgSO4 and concentrated in vacuo. Trituration of the resulting thick oil in n-heptane afforded cis-7-chloro-1,2,2a,3,4,9-hexahydro-8-methyl-9bH-cyclobuta[a]carbazole-9b-acetic acid, 1.28 g (50%), m.p. 189°-190° C.

Workup

  1. temperatureThe solution was refluxed for 30 minutes under nitrogen
  2. extractionextracted with 4×50 mL of ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29f98476e8c546889ebd4cb0617f5317
Source dataset
uspto-grants-1988_11
Patent number
US04783479

Reaction notes

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