Dimethyl Sulfoxide → 9-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)nonanal

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Reaction Conditions

Reaction Steps

DMSO (0.32 mL) and triethylamine (0.32 mL) were added to a solution of (9-(9-hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 2, step a) (0.32 g) in dichloromethane (5 mL). The mixture was cooled in an ice-salt bath and pyridine sulphur trioxide (0.36 g) was added. The reaction was stirred at −10° C. for 1 h then allowed to warm to room temperature and stirred for a further 3 h. The reaction was diluted with DCM (20 mL) then poured into brine (20 mL). The layers were separated and the organic layer washed with brine (20 mL), dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 47.5:47.5:5 isohexane:ethyl acetate:triethylamine to 95:5 ethyl acetate:triethylamine gradient to give the subtitled compound as a yellow oil. Yield 0.25 g.

Provenance & Evidence