Chemistry 251 Laboratory -- Spring 2000
Roefractine Project Home Page

Index

• 1999 Roefractine Project Home Page
• Students working on this project
• Table of Reagents and Amounts Available

Cabedo, N.; Protais, P.; Cassels, B.K.; Cortes, D. J. Nat. Prod., 1998 61, 709-712.

Dopamine is an important neurotransmitter. For example, cocaine acts by blocking dopamine uptake, while a deficiency of dopamine is associated with Parkinsonšs disease. As part of a series of studies aimed at better understanding the binding of alkaloids to dopamine receptors, (R)-(+)-nor-Roefractine was recently synthesized and its binding to dopamine receptors was studied. The synthesis starts with isovanillin which is protected as the benzyl ether before condensation with nitromethane to give the b--nitrostyrene derivative. Reduction to the amine, followed by reaction with 4-methoxyphenylacetyl chloride gives a compound that can be cyclized using POCl₃. Stereoselective reduction of the resulting cyclic imine followed by deprotection of the benzyl ether gives the desired (R)-(+)-nor-Roefractine.

The table below lists the chemicals that we will have available for this project. If you need something that is not on this list, consult with the mentor for your project. Also note the "Amount/group" column. This is the total amount of material available for each group to use on the project.

Reagent	Source	Amount/group	Location	Comments
3-hydroxy-4-methoxybenzaldehyde (isovanillin)	Aldrich Cat. # 14,368-5	5 g	TA room
Benzyl chloride	Aldrich Cat. # 18,555-8	25 mL	TA room	This material is a cancer suspect agent. It must be disposed of in a special container.
Nitromethane	Aldrich Cat. #36,055-4	50 mL	TA Room
4-Methoxyphenylacetic acid	Aldrich Cat. # M1,920-1	10 g	TA Room
Phosphorus oxychloride	Aldrich Cat # 20,117-0	10 g	TA Room