Figure 1 | Scientific Reports

Figure 1

From: The selective reversible FAAH inhibitor, SSR411298, restores the development of maladaptive behaviors to acute and chronic stress in rodents

Figure 1

Synthesis of SSR411298. The compound was prepared in 24% yield by carbamation of (trans)-3-[-5-(6-methoxynaphtalen-1-yl)-1,3-dioxan-2-yl]propanamine (6) with chloroacetamide. Compound (6) was obtained via the dioxane formation of 2-(6-methoxynaphtalen-1-yl)propan-1,3-diol (5) with 4,4-diethoxybutanamine, in 93% yield. Compound (5) was isolated in 42% yield from the reduction of diethyl-2-(6-methoxynaphtalen-1-yl)propanedioate (4). Compound (4) was synthesized by alkylation of ethyl-(6-methoxynaphtalen-1-yl)-acetate (3) with ethylcarbonate in 81% yield. Compound (3) was prepared in two steps, in 57% overall yield, consisting in a substitution-deshydratation sequence of 6-methoxy-1,2,3,4-tetrahydronaphtalen-1-one (1) with ethyl bromoacetate, followed by an oxydation of the naphtalene ring by DDQ.