tert-Butylsulfinamide, (R)-(+)- → HCID 86280124, compound

HRID 1774762Notes

Reaction equation

HRID 1774762 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[CH2:11][C:10](=O)[CH2:9]1>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[CH3:1][C:2]([S@:5]([N:7]=[C:10]1[CH2:11][O:8][CH2:9]1)=[O:6])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 150242543-Oxetanone

Product 1

HCID 86280124HCID 86280124, compoundYield 20.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Ti(OEt)4 (2.02 g, 7.53 mmol) in THF (20 mL) was added (R)-2-methylpropane-2-sulfinamide (0.854 g, 7.05 mmol) followed by oxetan-3-one (0.493 g, 6.84 mmol) in THF (5 mL) and the reaction mixture was heated to 50° C. over night. After cooling, the reaction mixture was diluted with EtOAc (50 mL) and a saturated solution of brine (20 mL) was slowly added under stirring. After 15 min, the mixture was filtered through a plug of Dicalite and washed with EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-heptane gradient to give the title compound (0.242 g, 20%) as a light yellow oil. MS: 176.2 (M+H+).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through a plug of Dicalite
  3. washwashed with EtOAc
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluting with a 0 to 40% EtOAc-heptane gradient

Sources & evidence

ORD record
ord-5a8259b09edd4c1db94851a0e7db0729
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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