Fumaric Acid → HCID 19095377, compound

Participants

Reaction Steps

6-[p-(Cyclopentyloxy)phenyl]-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine (1.5 g) was dissolved in a mixture of 100 ml of methanol, 10 ml of water and 25 ml of methylene chloride under argon. The solution was treated portionwise with 0.6 g of sodium borohydride while stirring and stirred at room temperature overnight. Thereafter, the solvent was removed in a vacuum, the residue was taken up in 100 ml of methylene chloride and washed with 100 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 60 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 1.6 g of brown oil, was dissolved in a 20-fold amount of hot ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 1.2 g (66%) of 6-[p-(cyclopentyloxy)phenyl]-1,2,3,4-tetrahydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (2:1); m.pt.: 172°-174° C. (dec.).

Provenance & Evidence