Sulfuric acid magnesium salt (1:1) → (S~2~S)-N-[(E)-Cyclobutylmethylidene]-2-methylpropane-2-sulfinamide

HRID 709423Notes

Reaction equation

HRID 709423 reaction equation
[CH:1]1([CH:5]=O)[CH2:4][CH2:3][CH2:2]1.[CH3:7][C:8]([S@@:11]([NH2:13])=[O:12])([CH3:10])[CH3:9].S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH:1]1(/[CH:5]=[N:13]/[S@:11]([C:8]([CH3:10])([CH3:9])[CH3:7])=[O:12])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 12431621Cyclobutanecarbaldehyde

Product 1

HCID 90236009(S~2~S)-N-[(E)-Cyclobutylmethylidene]-2-methylpropane-2-sulfinamideYield 106%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclobutanecarbaldehyde (1.0 g, 11.89 mmol, 1.00 equiv) in CH2Cl2 (10 mL) were added pyridinium p-toluenesulfonate (0.143 g, 0.57 mmol, 0.05 equiv), (S)-(−)-2-methylpropane-2-sulfinamide (1.22 g, 10.07 mmol, 0.85 equiv), and magnesium sulfate (7.14 g, 59.32 mmol, 5.00 equiv). The resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (silica gel, 30% EtOAc in petroleum ether) to provide 2.0 g (90%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.08 (d, J=10.8 Hz, 1H), 3.36-3.32 (m, 1H), 2.25-2.16 (m, 4H), 2.03-1.90 (m, 2H), 1.15 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by flash chromatography (silica gel, 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-5056f394e7bf4795bef62a45d54a1833
Source dataset
uspto-grants-2015_11
Patent number
US09181200B2

Reaction notes

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