Ammonium Chloride → (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 12.07 g .of (3aRS,6SR,7aSR)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-one in 50 cm3 of anhydrous tetrahydrofuran is run over a period of 15 minutes into a suspension, cooled to +5° C., of 2-methoxyphenylmagnesiumbromide (prepared from 6.4 cm3 of 2-bromoanisole and 1.24 g of magnesium) in 200 cm3 of anhydrous tetrahydrofuran. The reaction mixture is stirred at 20° C. for one hour, cooled to +5° C., treated with 250 cm3 of saturated aqueous ammonium chloride solution and extracted with 200 cm3 of ethyl acetate. The organic phase is washed with 300 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The oily residue is recrystallized from a mixture of ethyl acetate and diisopropyl ether, and the crystals are filtered, washed with diisopropyl ether, subjected to suction and then dried under reduced pressure (2.7 kPa). 11.38 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol are obtained in the form of white crystals. M.p.K =153° C.

Provenance & Evidence