Trifluoroacetic acid → 2-(3-(2-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)phenyl)acetaldehyde

Participants

Reaction Steps

A solution of (9-(2-(3-(2-hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 24, step c) (0.152 g) in DCM (5 mL) was cooled in ice-water and treated with trifluoroacetic acid (0.039 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.221 g) was added and the mixture was removed from the cooling bath and stirred at room temperature for 25 minutes. The reaction was quenched by the addition of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL), and the resulting two-phase mixture was stirred for 10 minutes. The mixture was then extracted twice with ethyl acetate, and the combined organic extracts washed with brine. Acetic acid (0.1 mL) was added, and then the acidified extracts were dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the subtitled compound as a brown gum. Yield 0.118 g.

Provenance & Evidence