Trifluoroacetic acid → 1,3-Dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

HRID 227255Notes

Reaction equation

HRID 227255 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[C:19]2([CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[NH:18][CH:17]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:16]1=[O:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:8]([N:15]1[C:19]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[NH:18][CH:17]([CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:16]1=[O:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68839424Tert-butyl 1,3-dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Product 1

HCID 688379421,3-Dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (68.5 g, 601 mmol) was added dropwise at 0° C. to a solution of tert-butyl 1,3-dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (13.5 g, 31.0 mmol) in CH2Cl2 (93 ml), and the mixture was stirred at this temperature for 15 min. After warming to RT, the reaction solution was stirred for a further 2.5 h. Subsequently, the reaction solution was adjusted to pH 7 to 8 using NaHCO3 solution, the organic phase was separated off, and the aqueous phase was extracted with CH2Cl2 (2×30 ml). The combined organic phase was dried over Na2SO4, filtered and the solvent was removed by distillation. Workup was carried out by means of column chromatography to give 1,3-dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one in a yield of 7.8 g (75% of theory).

Workup

  1. stirringthe reaction solution was stirred for a further 2.5 h
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×30 ml)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-2c33aa05b15a480b9b962d6e8d27af12
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Reaction notes

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