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Hydrogen Peroxide → 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine oxide hydrate

HRID 1963037
Notes
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Reaction equation

HRID 1963037 reaction equation
[OH:1]O.[F:3][C:4]1([F:12])[CH2:7][CH:6]([CH2:8][N:9]([CH3:11])[CH3:10])[CH2:5]1.O=O>CO.O.[Pd]>[OH2:1].[F:3][C:4]1([F:12])[CH2:7][CH:6]([CH2:8][N+:9]([O-:1])([CH3:11])[CH3:10])[CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 977OxygenHCID 579888311-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine

Product 1

HCID 866365581-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine oxide hydrate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst
HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

30% Aqueous H2O2 (18 mL) was added dropwise to a stirred solution of 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine (12 g, 80 mmol) prepared in Part B in methanol (100 mL) at 5 to 22° C. over 2 h. After stirring at RT for 20 h, additional 30% H2O2 (18 mL) was added. After 3 h, Pd black slurry (150 mg) in water (3 mL) was added to the stirred reaction mixture in small portions such that the temperature could be maintained between 5 to 25° C. with a cooling bath. The reaction mixture was stirred at RT for 1 h until the O2 evolution ceased. After filtration, the filtrate was concentrated in vacuo to give 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine oxide hydrate as a thick colorless oil (15 g, semisolid). 1H NMR (400 MHz, CD3OD) δ ppm 3.47 (2 H, d, J=5.29 Hz), 3.16 (6 H, s), 2.75-2.92 H, m), 2.42-2.58 (2 H,

Workup

  1. waitAfter 3 h
  2. temperaturecould be maintained between 5 to 25° C. with a cooling bath
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-80af201fd7554f22ab06844a7e7bc7d6
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415386B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes