Benzyl Bromide → HCID 10981812, compound

Participants

Reaction Conditions

Reaction Steps

7.9 cm3 of benzyl bromide are added to a solution, cooled to 0° C., of 21.7 g of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride in 300 cm3 of dichloromethane and 18.5 cm3 of triethylamine. After stirring for 1 hour at 0° C. and 2 hours at 20° C., the reaction mixture is washed with 50 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.04-0.06 mm, diameter 5 cm, height 40 cm), eluting under a nitrogen pressure of 0.6 bar with an ethyl acetate and cyclohexane mixture (75/25 by volume) and collecting fractions of 250 cm3. Fractions 3 to 6 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 22.1 g of (3aR, 7aR)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone are obtained in the form of a white solid; melting point 124° C. [α]20 =-279° C.

Provenance & Evidence