Acetic Acid → (9-(2-(3-(2-Hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Participants

Reaction Steps

A suspension of 2-(3-(2-hydroxyethyl)phenoxy)acetaldehyde (example 24, step b) (0.143 g) and (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 4, step h) (0.314 g) in methanol (10 mL) was treated with acetic acid (0.045 mL) and stirred at room temperature for 30 minutes. The mixture was cooled in ice-water, treated with sodium triacetoxyborohydride (0.254 g) and stirred over 3 days, allowing the ice-bath to expire. The resulting solution was purified by flash chromatography on silica eluted with 1:15:84 triethylamine:methanol:dichloromethane to afford the crude product (0.243 g). A second purification by flash chromatography on silica eluted with 1:5:94 triethylamine:methanol:dichloromethane afforded the slightly impure subtitled compound as a brown gum. Yield 0.122 g.

Provenance & Evidence