2,2,2-Trifluoroethanol → HCID 77699059, compound

Participants

Reaction Steps

To a stirring 2,2,2-trifluoroethanol (1.5 mL) solution of 3-nitromethyl-5-(propene-3-yl)cyclopentanone (mixture of isomers (0.366 g, 2.0 mmol)), under an inert atmosphere of nitrogen was added ammonium acetate (0.617 g, 8 mmol) and t-butylisonitrile (0.68 mL, 6.0 mmol) and the reaction mixture was stirred at room temperature for 2 days. The mixture was then diluted with methylene chloride (20 mL) and directly loaded onto a silica gel column (˜250 mL). The two cyclopentane-t-butyl carboxamide isomers with the acetamino and allyl substituents in syn conformation (isomers 1 and 2), elute first, followed by elution of isomer A (122 mg, 19%), and then isomer B (195 mg, 30%) as white solids.

Provenance & Evidence