Trifluoroacetic acid → 2,2,2-Trifluoro-1-[7-(phenylmethyl)-4,7-diazaspiro[2.5]oct-4-yl]ethanone

HRID 1876609Notes

Reaction equation

HRID 1876609 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[CH2:8]([N:15]1[CH2:22][C:19]2([CH2:21][CH2:20]2)[NH:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:8]([N:15]1[CH2:22][C:19]2([CH2:21][CH2:20]2)[N:18]([C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 585423257-Benzyl-4,7-diazaspiro[2.5]octane

Product 1

HCID 585424062,2,2-Trifluoro-1-[7-(phenylmethyl)-4,7-diazaspiro[2.5]oct-4-yl]ethanoneYield 102.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Anhydrous trifluoroacetic acid (8.50 ml, 61.1 mmol) was added dropwise to a methylene chloride (200 ml) solution of the compound (10.3 g, 50.9 mmol) obtained in Step 3 above and triethylamine (17 ml, 122 mmol) with ice cooling and the resulting mixture was stirred at the same temperature for 1 hour. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, the resulting mixture was diluted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.5 g, 100%) as a colorless oil.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-546dd40b1bf6455ba49dfd81afdbaa98
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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