Dichloromethane → HCID 18932923, compound

Participants

Reaction Steps

A solution of the product from Example 2 (0.50 g) and triethylamine (0.80 mL) in dichloromethane (5 mL) was cooled with an ice-water bath. To the solution was added triphosgene (0.17 g) in dichloromethane (1 mL) over 2 minutes. A dichloromethane (1 mL) wash of the addition syringe was also added to the reaction mixture. The mixture was stirred at ice bath temperature for 30 minutes. Solid 4-pyridinemethanol (0.38 g) was added in a single portion to the mixture. Stirring was continued at ice bath temperature for 90 minutes, and the solution was allowed to warm to room temperature overnight. The mixture was diluted with dichloromethane, washed (water), dried and evaporated to a brown foam (0.60 g). This material was purified by chromatography, with chloroform:methanol (50:1) as the eluent, to give the title compound (0.11 g) as a yellow solid; TLC: Rf =0.35, methanol:chloroform (5:95); NMR: 0.85 (d,6, J=7), 1.17 (s,1), 1.17-1.80 (m, 1), 2.68 (t,1), 4.48 (s,2), 5.24 (s,2), 7.44-7.56 (m,7), 8.28 (d,1, J=5.5), 8.47 (s,1), 8.58 (dd,2), 9.23 (s,1); MS: m/z=562(M+1).

Provenance & Evidence