8-Trifluoroacetyl-1,4-dioxa-8-azaspiro[4.5]decane → 8-(2,2,2-Trifluoroethyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1985791Notes

Reaction equation

HRID 1985791 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>C1COCC1.B.CSC>[F:15][C:12]([F:13])([F:14])[CH2:11][N:8]1[CH2:9][CH2:10][C:5]2([O:1][CH2:2][CH2:3][O:4]2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 29919218-Trifluoroacetyl-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 670071628-(2,2,2-Trifluoroethyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 100.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12423031(Dimethyl sulfide)trihydroboronSolvent

Procedure

In the solution of 1-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-2,2,2-trifluoroethanone (20 g, 83.7 mmol) in THF, borane-methyl sulfide complex (83.7 mL, 2M solution in THF) was added at 0° C. After refluxing the reaction mixture for 12 h, the reaction was cooled and quenched with MeOH. After removal of THF, the residue was extracted with ethyl acetate and washed with brine, dried with MgSO4 and concentrated to give 8-(2,2,2-trifluoroethyl)-1,4-dioxa-8-aza-spiro[4.5]decane (19 g) was obtained.

Workup

  1. temperatureAfter refluxing the reaction mixture for 12 h
  2. temperaturethe reaction was cooled
  3. customquenched with MeOH
  4. customAfter removal of THF
  5. extractionthe residue was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-debcee8a4e55476b9dcf9018f26b8492
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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