Dimethylamine → Tert-butyl 1-(dimethylamino)-3-(3-hydroxyphenyl)-1-oxopropan-2-ylcarbamate

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Reaction Steps

The 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoic acid (0.89 g, 3.1 mol) was treated with N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.8 g, 4.6 mmol), N,N-diisopropylethylamine (1.6 mL, 9.3 mmol) and 2 M dimethylamine in THF (3.0 mL, 6.0 mmol), in N,N-dimethylformamide (20 mL) at r.t. The reaction was complete after stirring for 2 h. This was taken up in ethyl acetate and washed with 1 N HCl, brine, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oily residue. The product was purified by flash chromatography on a silica gel column eluting hexane: ethyl acetate gradient to give tert-butyl 1-(dimethylamino)-3-(3-hydroxyphenyl)-1-oxopropan-2-ylcarbamate (0.75 g, 78%) as an off white solid. Analytical LCMS (M+H-Boc)+: m/z=208.9.

Provenance & Evidence