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

HRID 1615157Notes

Reaction equation

HRID 1615157 reaction equation
[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+]>O1CCCC1.O.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[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

Participants

7

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-sulfinamide

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methly-2-propanesulfinamide (7.4 g) is added to a solution of 1,4-dioxa-spiro[4.5]decan-8-one (10.0 g) and titanium tetraisopropoxide (37.9 mL) in tetrahydrofuran (130 mL) at room temperature. After stirring the solution at room temperature overnight, it is poured into a stirred saturated solution of NaHCO3 in water. The resulting mixture is filtered over Celite and the remainder in the filter is thoroughly washed with ethyl acetate. The organic phase of the filtrate is separated, washed with brine, and dried (MgSO4). The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 1:2→0:1) to give the title compound as a colorless solid. Yield: 7.0 g (42% of theory); TLC [silicagel, cyclohexane/ethyl acetate 1:2]: rf=0.5; Mass spectrum (ESI+): m/z=260 [M+H]+.

Workup

  1. filtrationThe resulting mixture is filtered over Celite
  2. washthe remainder in the filter is thoroughly washed with ethyl acetate
  3. customThe organic phase of the filtrate is separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed (cyclohexane/ethyl acetate 1:2→0:1)

Sources & evidence

ORD record
ord-e769a5fe2cf748cbb37431c8aecd3f0f
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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