Hydrochloric Acid → HCID 86692748, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 8 (1 g, 4.69 mmol), 1-aminocyclopropanecarbonitrile hydrochloride (743 mg, 6.27 mmol) and sodium 2-ethylhexanoate (1.22 g, 7.12 mmol) in water (7 mL) was stirred for 2 days at 50° C. The reaction was acidified with 1N aqueous hydrogen chloride solution, saturated with sodium chloride and stirred with ethyl acetate for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica using a gradient of methylene chloride to a mixtures of methylene chloride and methanol (v:v 19:1) to yield the amide 9 as an off-white solid (763 mg, 55.1%). MS ISN (m/e): 294.3 (100) [(M−H)]+.

Provenance & Evidence