(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one → 8-[(2S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-17, 10 mg, 0.040 mmol) in ethanol (2 mL) in a microwave tube was added (S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one (I-4A, 9.9 mg, 0.052 mmol)) and the resulting solution was heated at 140° C. in microwave for 3 h. After concentration, the residue was purified by preparative TLC using 30% methanol/ethyl acetate to give the title compound. LC/MS, (M+1)+: 441.00, 1HNMR (500 MHz, CDCl3), δ7.840-7.804(m, 2H), 5.304-5.240(m, 4H), 5.134-5.107(m, 1H), 4.066-4.038(t, J=7.1Hz, 2H), 3.185-3.161(m, 1H), 2.8885-2.862(m, 1H), 2.629-2.568 (m, 2H), 2.462-2.416(m, 1H), 2.305 (s, 3H), 2.344-2.323(m, 1H), 2.197-2.158(t, J=7.1 Hz, 2H), 2.108-2.033(m, 5H), 1.661-1.604(m, 2H).

Provenance & Evidence