Isopropyl Acetate → methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of (1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one (725 g, 6.64 mol) in MeOH (2.2 L) was stirred in an ice bath to 0° C. Thionyl chloride (290 mL, 3.99 mol) was added dropwise over a 2.25 h period while keeping the temperature below 13° C. The reaction was stirred for 2 h at 8° C. Isopropyl acetate (16.3 L) was added and the slurry stirred for 1 h. The solid was filtered with a Buchner funnel, washed with isopropylacetate (˜1 L) and the solid was allowed to air-dry overnight to afford an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=8.44 (br. s., 3H), 5.99-6.16 (m, 1H), 5.90 (dt, J=2.4, 5.3 Hz, 1H), 4.17 (br. s., 1H), 3.56-3.79 (m, 4H), 2.56 (m, 1H), 1.84-2.04 (m, 1H).

Provenance & Evidence