4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 8-[(2R)-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 Steps

A solution of 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-17, 6.00 g, 24.0 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (1-4B, 5.93 g, 31.2 mmol) in ethanol (20 mL) in a sealed tube was heated at 95° C. overnight. After concentration, the residue was purified on silica gel column using methanol/dichloromethane, then precipitated from methanol to give the title compound. LC/MS, (M+1)+: 440.93. 1HNMR (500 MHz, CDCl3), δ7.845-7.809 (m, 2H), 5.290-5.278 (m, 4H), 5.139-5.112 (m, 1H), 4.072-4.044 (t, J=7.1 Hz, 2H), 3.190-3.167 (m, 1H), 2.876-2.859 (m, 1H), 2.636-2.604 (m, 2H), 2.468-2.421 (m, 1H), 2.311 (s, 3H), 2.350-2.328 (m, 1H), 2.193-2.165 (t, J=7.1 Hz, 2H), 2.101-2.039 (m, 5H), 1.668-1.618 (m, 2H).

Provenance & Evidence