HCID 67216429, compound → HCID 58557162, compound

Participants

Reaction Steps

To a solution of ethyl 2-((3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentylidene)acetate (0.160 g, 0.754 mmol) in DCM (3 mL) was added Crabtree's catalyst (0.030 g, 0.038 mmol). The reaction mixture was sparged with hydrogen for about 5 min and an atmosphere of hydrogen was maintained via balloon. After about 24 h, the reaction mixture was concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane (30-80%) to provide ethyl 2-((1R,3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentyl)acetate (0.140 g, 87%) as an oil. 1H NMR (400 MHz, CDCl3) δ 4.12 (q, J=7.1 Hz, 2H), 3.71-3.64 (dd, J=10.5, 8.0 Hz, 1H), 3.47 (dd, J=10.5, 8.0 Hz, 1H), 2.55-2.41 (m, 1H), 2.32 (d, J=6.7 Hz, 2H), 2.02-1.89 (m, 1H), 1.88-1.76 (m, 1H), 1.70-1.60 (m, 1H), 1.48-1.33 (m, 4H), 1.26 (t, J=7.1 Hz, 3H), 1.22-1.07 (m, 1H), 0.90 (t, J=7.4 Hz, 3H).

Provenance & Evidence