2-Methoxyphenylacetic acid → (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol

Participants

Reaction Conditions

Reaction Steps

2.3 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added to a solution of 3 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol and 1.8 g of (2-methoxyphenyl)acetic acid in 60 cm3 of dichloromethane. The reaction mixture is stirred at 20° C. for 20 hours and then washed with 30 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 (particle size 0.06-0.20 mm, height [lacuna]cm) in ethyl acetate and then in a mixture of ethyl acetate and methanol (95:5 by volume). Drying under reduced pressure gives a white solid which, after recrystallization from a mixture of ethyl ether and acetonitrile, gives 2.1 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol in the form of white crystals. M.p.=162° C.

Provenance & Evidence