Borane;tetrahydrofuran → HCID 68442167, compound

Participants

Reaction Steps

To a solution of 0.10 g of (2S,4R,5R)-2-carboxymethyl-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1 carboxylic acid benzyl ester (from example 9b) in 8.0 ml of tetrahydrofuran are added 0.31 ml of a solution of borane tetrahydrofuran (1M) at 50° C. The reaction mixture is stirred for 2 hours at this temperature, allowed to cool to room temperature and quenched by addition of methanol. The mixture is concentrated under reduced pressure and the obtained residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a colourless oil. Rf=0.50 (EtOAc-heptane 5:1); Rt=4.95.

Provenance & Evidence