Trifluoroacetic acid → 3-Methyl-3,9-diazaspiro[5.5]undecane

HRID 548942

Reaction equation

HRID 548942 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16](C)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:6][N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58808179HCID 58808179, compound

Product 1

HCID 218132933-Methyl-3,9-diazaspiro[5.5]undecaneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

9-Methyl-3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (435 mg, 1.62 mmol) was dissolved in dichloromethane (11 mL) and cooled on ice. Trifluoroacetic acid (4 mL) in dichloromethane (5 mL) was added and the reaction mixture was stirred at room temperature for 2 h. Evaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether gave a foam which was dissolved in dichloromethane, and sodium hydroxide (2 N) was added. The aqueous phase was extracted five times with dichloromethane. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 214 mg (78%) of 3-methyl-3,9-diaza-spiro[5.5]undecane.

Workup

  1. temperaturecooled on ice
  2. customEvaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether
  3. customgave a foam which
  4. extractionThe aqueous phase was extracted five times with dichloromethane
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-34833a95099246088d70e08d92898144
Source dataset
uspto-grants-2011_05
Patent number
US07943630B2

Linked notes

Loading…