Water → HCID 59578062, compound

Participants

Reaction Steps

2-(4-Iodo-phenyl)-8-(2-trifluoromethoxy-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.01 g), product of example 104), was taken up in a mixture of ethanol (1 ml), water (1 ml) and toluene (8 ml), treated with K2CO3 (0.071 g) and (E)-2-(3-methoxypropenyl)-4,4,5,5-tetramethyl-(1,3,2)-dioxaboroane and stirred 30 minutes at RT under an argon atmosphere. Then tetrakis(triphenylphosphine)palladium(0) (0.02 g) was added and the mixture was heated at 85° C. for 4 h. It was then cooled to RT, partitioned between AcOEt and water, the layers were separated, the organic layer was dried over sodium sulphate, the solvent was removed in vacuo and the residue chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%) to give the desired 2-[4-((E)-3-methoxy-propenyl)-phenyl]-8-(2-trifluoromethoxy-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.077 g) as an off white solid. MS (ESI): 525.16 (MH+).

Provenance & Evidence