Water → Cyclopentanone

Participants

Reaction Steps

4-Toluenesulphonic acid monohydrate (1.7 g, 9.2 mmol) was added to a stirred solution of (2S)-2-tert-butoxycarbonylamino-3-phenylpropionic acid 2,2-dimethoxycyclopentyl ester (36 g, 91.6 mmol) in acetone (450 ml) at ambient temperature. The solution was stirred for 3 days then water (600 ml) and saturated aqueous sodium hydrogen carbonate solution (200 ml) were added, then the product was extracted into ethyl acetate (600 ml). The aqueous phase was extracted with ethyl acetate (2×400 ml), then the combined ethyl acetate solutions were washed with saturated aqueous sodium chloride solution (2×150 ml), dried (Na2SO4) and the solvent removed in vacua. The residue (18.05 g) was purified by flash chromatography over silica gel eluting with a gradient of heptane:ethyl acetate 3:1→2:1. Appropriate fractions were combined and the solvents removed in vacuo to leave (2S)-2-tert-butoxycarbonylamino-3-phenylpropionic acid 2-oxocyclopentyl ester as a colourless oil (18.05 g, 40% from cyclopentanone). TLC (single UV spot, Rf=0.25, heptane:ethyl acetate 7:3), analytical HPLC with main broad peak Rt=17.9-19.2 mins, HPLC-MS (main broad UV peak with Rt=9.04-9.24 mins, 248.1 [M−Boc+2H]+, 370.2 [M+Na]+, 717.3 [2M+Na]+).

Provenance & Evidence