Sulfuric Acid → 3-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

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Reaction Steps

1-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone (0.63 g, 2 mmol) was initially introduced into water (14 ml) and sulfuric acid (95%, 14 ml) was added. The reaction mixture was refluxed for 5 hours, cooled with an ice bath, neutralized with sodium hydroxide solution (5 mol/l) and concentrated in vacuo. Ethyl acetate (10 ml) was added to the residue and the suspension was stirred at room temperature for 30 minutes. The precipitate was filtered out with suction and the mother liquor was extracted with ethyl acetate (4×20 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The yield was 0.34 g (84%). [The regiochemistry was assigned in analogy to AM1-AM4.]

Provenance & Evidence