Fluoromethyl Phenyl Sulfone → N-(1-(fluoro(phenylsulfonyl)methyl)cyclobutyl)-2-methylpropane-2-sulfinamide

HRID 1777309Notes

Reaction equation

HRID 1777309 reaction equation
[F:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].C([Li])CCC.[C:17]1(=[N:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[CH2:20][CH2:19][CH2:18]1>O1CCCC1>[F:1][CH:2]([S:3]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:5])[C:17]1([NH:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 2759036Fluoromethyl Phenyl SulfoneHCID 67250305N-cyclobutylidene-2-methylpropane-2-sulfinamideHCID 178418339Butyllithium

Product 1

HCID 90089429N-(1-(fluoro(phenylsulfonyl)methyl)cyclobutyl)-2-methylpropane-2-sulfinamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ((fluoromethyl)sulfonyl)benzene (5.0 g, 28.7 mmol) in tetrahydrofuran (100 mL) at −78° C. under argon was added n-butyl lithium (18.0 mL, 28.7 mmol) and the reaction mixture was stirred for 40 minutes at this temperature. N-cyclobutylidene-2-methylpropane-2-sulfinamide (3.23 g, 18.7 mmol) was added to the mixture at −78° C. and the reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was quenched by the addition of water and extracted 3 times with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to afford a brown oil. The residue was purified by flash column chromatography on silica (eluent: heptane:ethyl acetate, 3:2 to 2:3) to give N-(1-(fluoro(phenylsulfonyl)methyl)cyclobutyl)-2-methylpropane-2-sulfinamide (3.00 g, 33%) as a yellow oil.

Workup

  1. stirringstirred overnight
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionextracted 3 times with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford a brown oil
  8. customThe residue was purified by flash column chromatography on silica (eluent: heptane:ethyl acetate, 3:2 to 2:3)

Sources & evidence

ORD record
ord-2c032e2f563b48adbf6f64e4aef836c7
Source dataset
uspto-grants-2016_02
Patent number
US09266857B2

Reaction notes

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