Hydrochloric Acid → HCID 19029016, compound

HRID 1781508Notes

Reaction equation

HRID 1781508 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:15](=[CH:16][CH:17]=1)[C:14](=O)[C:8]1([CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)[CH2:7][CH2:6]2.C([SiH](CC)CC)C.[ClH:26]>FC(F)(F)C(O)=O.O>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C:8]1([CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 19028852HCID 19028852, compound

Product 1

HCID 19029016HCID 19029016, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

In 30 ml of trifluoroacetic acid was dissolved 6.57 g of 3,4-dihydro-6-methoxyspiro[naphthalene-2(1H),2'-piperidin]-1-one followed by addition of 8.5 ml of triethylsilane and the mixture was stirred for 1 hour. This reaction mixture was poured portionwise in water. To this was added 1N-hydrochloric acid and the mixture was washed with hexane. The aqueous layer was made basic to 1N-aqueous sodium hydroxide and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. The group was treated with 7.0 ml of 4N-methanolic hydrochloric acid to give a solid. This solid was recrystallized from methanol-ether to provide 5.09 g of white crystals.

Workup

  1. washthe mixture was washed with hexane
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off
  6. additionThe group was treated with 7.0 ml of 4N-methanolic hydrochloric acid
  7. customto give a solid
  8. customThis solid was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-686546873c7d4c56ba5142ce531de9e0
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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