Sulfuric acid magnesium salt (1:1) → N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

HRID 1040213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040213
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[C:12]2([CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C(#N)C>[O:8]1[C:12]2([CH2:17][CH2:16][C:15](=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1

Komponenten

8

Edukt 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Produkt 1

HCID 59733754N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamideAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524Titanium tetraethoxideKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-(−)-2-methyl-2-propanesulfinamide (854 mg, 7 mmol) and 1,4-dioxaspiro[4,5]decan-8-one (1 g, 6.40 mmol) in tetrahydrofuran (13 mL) was added titanium(IV) ethoxide (5.11 mL, 16 mmol). The mixture was stirred for 4 h at room temperature, poured over stirring saturated aqueous sodium bicarbonate (10 mL) and acetonitrile (10 mL), and stirred for 20 minutes. Magnesium sulfate was added and the mixture was stirred for 20 minutes, filtered over celite and concentrated. The residue was purified by column chromatography on silica gel (10:90 to 70:30 ethyl acetate:hexanes gradient) to afford N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide (466 mg, 1.8 mmol, 28% yield) as a white solid. MS ESI: [M+H]+ m/z 260.

Aufarbeitung

  1. additionpoured
  2. stirringstirred for 20 minutes
  3. stirringthe mixture was stirred for 20 minutes
  4. filtrationfiltered over celite and
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (10:90 to 70:30 ethyl acetate:hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-6758dfb09dc34d3c9474e399513a7377
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551984B2

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