Sodium Bicarbonate → N-(1-(fluoromethyl)cyclobutyl)-2-methylpropane-2-sulfinamide

HRID 1777310Notes

Reaction equation

HRID 1777310 reaction equation
[F:1][CH:2](S(C1C=CC=CC=1)(=O)=O)[C:3]1([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH2:6][CH2:5][CH2:4]1.C([O-])(=O)C.[Na+].[Mg].C(=O)([O-])O.[Na+]>CN(C)C=O.C(O)(=O)C.O>[F:1][CH2:2][C:3]1([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5462224MagnesiumHCID 90089429N-(1-(fluoro(phenylsulfonyl)methyl)cyclobutyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 90089490N-(1-(fluoromethyl)cyclobutyl)-2-methylpropane-2-sulfinamideYield 62.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(1-(fluoro(phenylsulfonyl)methyl)cyclobutyl)-2-methylpropane-2-sulfinamide (1.50 g, 4.32 mmol) in N,N-dimethylformamide (270 mL) was added a buffer solution of sodium acetate (22.6 g, 276 mmol) in acetic acid (34.6 mL) and the reaction mixture was stirred for 15 minutes at room temperature. Magnesium turnings (6.92 g, 289 mmol) were added and the mixture stirred at 65° C. for 24 hours. The mixture was treated with water and saturated aqueous sodium hydrogen carbonate and extracted 3 times with ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated to give a yellow oil. The residue was purified by flash column chromatography on silica (eluent: heptane:ethyl acetate 1:1 to 0:1) to give N-(1-(fluoromethyl)cyclobutyl)-2-methylpropane-2-sulfinamide (560 mg, 53%) as a pale yellow oil.

Workup

  1. stirringthe mixture stirred at 65° C. for 24 hours
  2. extractionextracted 3 times with ethyl acetate
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customThe residue was purified by flash column chromatography on silica (eluent: heptane:ethyl acetate 1:1 to 0:1)

Sources & evidence

ORD record
ord-a242c773ccb5420492a39a09639912be
Source dataset
uspto-grants-2016_02
Patent number
US09266857B2

Reaction notes

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