Question

Two stereoisomers are obtained from the reaction of cyclopentene oxide and dimethylamine. The R,R-isomer is used in the manufacture of eclanamine, an antidepressant. What other isomer is obtained?
10. TUNNIS ОН R,R-isomer eclanamine

Answer 1

. The reaction is, + Meyron *** Mit L-AAH 1. OH N-ne Me : (5,5) isomer OH mére RR isomer 31. org (5) OH OH on Amet me 2 oht me Name Seine so, the other isomer is (s) isomer.

The oxygen of the epoxide adds syn to the alkene (Cyclo Pene tene). AS a In the one of the Product (oiven the -oh group is in up position so we conclude that oxygen adds to the tope face of the alkene. There for the epoxide has a Chiral centre. The Me, NH is nucleophile and it attack the carbon bound to an oxygen SN2 fashion. This cause pind opening of the epoxide and the -OH and-MeN group in an . 1. anti relationship: . The amine is able to attack either side of the epoxide to give the (RiR) and isomers. This two are enantiomers. so, the other isomer is (ss) o nome Olme