Potassium Cyanide → (3aRS,4RS,6RS,7aSR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-tert-butyloxycarbonylperhydroisoindol-4-ol

Participants

Reaction Conditions

Reaction Steps

40 g of potassium cyanide are added carefully to a solution of 215 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-tert-butyloxycarbonyl-6-tosyloxymethylperhydroisoindol-4-ol in 800 cm3 of dimethyl sulphoxide. The reaction mixture is stirred at 50° C. for 20 hours, diluted with 1 liter of water and extracted with twice 200 cm3 and then 100 cm3 of ethyl acetate. The combined organic extracts are washed with twice 500 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is recrystallized from 200 cm3 of ethyl ether, and the crystals are washed with the same solvent, drained and then dried under reduced pressure (2.7 kPa). 142 g of (3aRS,4RS,6RS,7aSR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-tert-butyloxycarbonylperhydroisoindol-4-ol are obtained in the form of a white solid. M.p.K =149° C.

Provenance & Evidence