Acetic Acid → 4-Benzyloxy-1-[2-(3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-ethyl]-1H-pyridin-2-one

참여 물질

반응 단계

To 2.00 g (5.15 mmol) 4-benzyloxy-1-[2-oxo-2-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-ethyl]-1H-pyridin-2-one (preparation 22.3) in 20 mL THF is added 0.41 mL (5.51 mmol) aqueous 37% formaldehyde solution. The mixture is acidified (pH 4-5) with acetic acid and then 1.27 g (5.97 mmol) sodium triacetoxy-borohydride is added. The reaction mixture is stirred overnight at RT, diluted with aqueous saturated NaHCO3-solution until pH 7 and THF is evaporated. The residue is diluted with EtOAc, the layers are separated and the organic phase is concentrated. The residue is elutriated in tert-butylmethylether and is collected by filtration. The residue is dissolved in DMF and purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

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