Sodium Bicarbonate → N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

HRID 132095

Reaction equation

HRID 132095 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:12][C:13]([S:16]([NH2:18])=[O:17])([CH3:15])[CH3:14].C([O-])(O)=O.[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[N:18][S:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 59733754N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamideYield 45.8%

Reagents, catalysts & solvents 1

HCID 76524Titanium tetraethoxideCatalyst

Procedure

An oven dried round-bottom flask was cooled to room temperature by flushing with N2(g) for 30 min. 1,4-Dioxa-spiro[4.5]decan-8-one (1.35 g, 8.66 mmol) (dissolved in 12 mL THF), 2-Methyl-propane-2-sulfinic acid amide (1.0 g, 8.25 mmol) (dissolved in THF), and titanium(IV) ethoxide (3.77 g, 16.50 mmol) were added. The reaction was stirred for 4 h at room temperature. To the mixture was added 15 mL saturated NaHCO3 followed by filtration and an EtOAc rinse. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure yielding 0.98 g of Compound 15.

Workup

  1. customby flushing with N2(g) for 30 min
  2. filtrationfollowed by filtration
  3. washan EtOAc rinse
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-daa05a7ddeb148df9d3a671b4d156bfb
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Linked notes

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