Trifluoroacetic acid → 2-(3-((4-(Benzo[b]thiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)-2-fluorophenyl)acetaldehyde

Participants

Reaction Steps

Dess-Martin periodinane (0.282 g) was added to a stirred solution of benzo[b]thiophen-2-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 79, step b) (0.240 g) and trifluoroacetic acid (0.059 mL) in DCM (5 mL). After 1 h, ethyl acetate (30 mL) was added followed by a mixture of saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL). The reaction mixture was shaken well and separated. The ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine. Acetic acid (0.08 mL) was added, then the solution was dried over sodium sulphate, filtered and evaporated in vacuo (bath temperature ˜30° C.) to give the subtitled compound as a gum. Yield 0.24 g. Used directly.

Provenance & Evidence