Dimethyl Sulfoxide → HCID 58691210, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (N-(cyclopropylmethyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(1-phenylprop-2-en-1-yl)pent-4-enamide (4c) (210 mg) dissolved in Toluene (25 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (21 mg) and the reaction mixture was stirred at 80° C. for 1 h, then cooled to RT. DMSO (0.1 mL) was added to the reaction mixture which was stirred for 2 h, then concentrated. The crude product was directly purified via flash chromatography (gradient—5%, 10% and 15% EtOAc/hexanes) to give a diastereomeric mixture (1.5:1) of the title compound (128 mg, 66%). 1H NMR (300 MHz, CDCl3) δ 0.03-0.09 (m, 1H), 0.22-0.34 (m, 2H), 0.46-0.57 (m, 1H), 0.66-0.72 (m, 0.6H), 1.03-1.09 (m, 0.4H), 2.42-2.48 (m, 1H), 2.98 (dd, 0.6H), 3.20 (dd, 0.4H), 3.55 (dd, 0.6H), 3.61-3.74 (m, 1H), 3.94 (dd, 0.4H), 5.09 (dd, 0.4H), 5.28 (bd, 0.4H), 5.57 (dd, 0.6H), 5.77(d, 0.6H), 6.00-6.08 (m, 1H), 6.26-6.35 (m, 1H), 7.35-7.48 (m, 5H), 7.65-7.88 (m, 4H). MS APCI, m/z=387 (M+1). LC/MS 2.66 min., Method A.

Provenance & Evidence