Ethyl Acetate → 9-(3,4-Dichlorophenyl)-3-azaspiro[5.5]undec-8-ene

HRID 419275Notes

Reaction equation

HRID 419275 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)(O)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.[OH-].[Na+]>FC(F)(F)C(O)=O>[Cl:27][C:22]1[CH:21]=[C:20]([C:16]2[CH2:17][CH2:18][C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:14][CH:15]=2)[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 666507759-(3,4-Dichloro-phenyl)-9-hydroxy-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester

Product 1

HCID 160063269-(3,4-Dichlorophenyl)-3-azaspiro[5.5]undec-8-eneYield 104.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

9-(3,4-Dichloro-phenyl)-9-hydroxy-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (547 mg, 1.32 mmol) was dissolved in trifluoroacetic acid (25 mL) and heated to reflux over night. Ethyl acetate was added and the reaction mixture was basified with sodium hydroxide (2 N). The aqueous phase was extracted three times with ethyl acetate and the combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 410 mg (100%) of 9-(3,4-dichloro-phenyl)-3-aza-spiro[5.5]undec-8-ene as a white gum.

Workup

  1. temperatureheated
  2. temperatureto reflux over night
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-44bb397814ec4205a8727e70f730e19a
Source dataset
uspto-grants-2012_01
Patent number
US08093388B2

Reaction notes

Loading…