Lithium Bromide → (3aRS,4RS,6SR,7aSR)-6-bromomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol

Participants

Reaction Steps

A solution of 1.16 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol and 0.345 g of anhydrous lithium bromide in 60 cm3 of acetone is heated at reflux for 18 hours and then concentrated to reduced volume (10 cm3). Following the addition of 20 cm3 of water, the mixture is subjected to extraction with 40 cm3 of ethyl acetate, washed with 20 cm3 of water and then dried over magnesium sulphate. After concentration to dryness under reduced pressure (2.7 kPa), the residue is washed with 20 cm3 of ethyl ether, drained and dried under reduced pressure (2.7 kPa). 0.66 g of (3aRS,4RS,6SR,7aSR)-6-bromomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol is obtained in the form of a white solid. M.p.K =191° C.

Provenance & Evidence