Sodium Bicarbonate → HCID 67354698, compound

Participants

Reaction Conditions

Reaction Steps

4-[(3-hydroxy-1-pyrrolidinyl)sulfonyl]benzonitrile 23a (17.0 g, 67.3 mmol) was dissolved in DCM (300 ml) and treated at room temp with PS-TEMPO (capacity: 1.17 mmol/g, 400 mg, 0.74 mmol). Then 5% aqueous sodium hydrogencarbonate solution (150 ml) was added and the mixture stirred vigorously while cooling to 10° C. Aqueous sodium hypochlorite (titrated at 7.0 wt % NaOCl*; 77.6 ml, 93.0 g, 87.5 mmol) was added over 40 min, maintaining the temperature below 10° C. Cooling was removed and the reaction mixture stirred vigorously. TLC after 2 h showed no starting material, therefore the stirring was stopped and layers separated. The aqueous layer was extracted with DCM (2×30 ml), and the combined organic layers washed with saturated aqueous sodium thiosulphate (75 ml) then water (150 ml). Each of these aqueous layers were back-extracted with DCM (30 ml) and combined with the main organic extract, which was then filtered through a cotton wool plug and evaporated to dryness, yielding 14.3 g (85%) ketone 4-[(3-oxo-1-pyrrolidinyl)sulfonyl]benzonitrile 23b.

Provenance & Evidence