Ammonium Chloride → HCID 15289535, compound

Participants

Reaction Steps

A suspension of 10.78 g of phenylmagnesium bromide in 65 cm3 of diethyl ether is added dropwise to a solution of 11.66 g of (3aS,7aS)-7,7-diphenyl-2-tert-butoxycarbonylperhydroisoindol-4-one in 70 cm3 of dry tetrahydrofuran at room temperature, while stirring. The reaction mixture is stirred at room temperature for 24 hours, refluxed for 5 hours, subsequently treated with 250 cm3 of a saturated aqueous solution of ammonium chloride, diluted with 200 cm3 of ethyl acetate, washed with 200 cm3 of water (twice) and then with 200 cm3 of a saturated aqueous solution of sodium chloride, and is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 5.3 cm, height 31.5 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume) and collecting fractions of 100 cm3. Fractions 23 to 48 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 5.75 g of (3aS,4S,7aS)-4,7,7-triphenyl-2-tert-butoxycarbonylperhydroisoindol-4-ol are obtained in the form of a pale yellow foam.

Provenance & Evidence