HCID 57296559, compound → HCID 86331931, compound

Participants

Reaction Steps

A solution 3-aza-2-oxabicyclo[2.2.1]heptane-3-carboxylic acid, (phenylmethyl) ester (0.5 g) in glacial acetic acid (0.5 ml) was added to a stirred suspension of powdered zinc (0.35 g) in a mixture of acetic acid and water (1:1; 4 ml), and the mixture was stirred at 60° for 7.5 h. Additional zinc powder (0.14 g) and acetic acid (1 ml) were added and stirring was continued for a further 16.5 h. After cooling to room temperature, the mixture was filtered and the excess of zinc washed with 2M hydrochloric acid (20 ml). The combined filtrate and washings were neutralised with 8% sodium carbonate and extracted into ethyl acetate (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried and concentrated in vacuo. Purification by FCC eluting with ethyl acetate: cyclohexane (1:1) gave an oil (120 mg) which solidified upon standing and was recrystallised from cyclohexane to give the title compound (70 mg), m.p. 62°-63°.

Provenance & Evidence