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

Participants

Reaction Conditions

Reaction Steps

A mixture of 6.05 g of (3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol, 0.6 g of 10% palladium on carbon and 300 cm3 of ethanol is heated to 60° C. Hydrogen is bubbled through for 3 hours, and then the reaction mixture is left at 20° C. for 20 hours and then purged with a stream of nitrogen, filtered and concentrated under reduced pressure (2.7 kPa). 5.7 g of (3aRS,4RS,6SR,7aSR)-6-aminomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol are obtained in the form of a thick white foam.

Provenance & Evidence