Hydrochloric Acid → 3-Benzyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

HRID 458154Notes

Reaction equation

HRID 458154 reaction equation
C(OC([N:8]1[CH2:31][CH2:30][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][N:13]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:12]2=[O:29])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C.CCOCC>[CH2:22]([N:13]1[C:12](=[O:29])[C:11]2([CH2:30][CH2:31][NH:8][CH2:9][CH2:10]2)[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 223806103-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

Product 1

HCID 184417443-Benzyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.16 g (5.12 mmol) 3-benzyl-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester in 43 ml ethyl acetate and 25 ml of a saturated solution of HCl in ether was stirred at ambient temperature for 90 min. The resulting suspension was filtered, the filtrate was dissolved in water and treated with saturated NaHCO3 and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to provide 3-benzyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one as a brown solid; MS (ISP): 322.5 MH+.

Workup

  1. filtrationThe resulting suspension was filtered
  2. dissolutionthe filtrate was dissolved in water
  3. additiontreated with saturated NaHCO3
  4. extractionextracted with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7a24affeddd64c3882fbe77061762f0e
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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