Methanol → (S)-2-Hydroxy-N-methyl-2-phenylacetamide

Participants

Reaction Steps

Methyl (S)-(+)-mandelate 36 (4.60 g, 27.7 mmol, 1.0 eq) was added to a 2M solution of methylamine in methanol, (70 mL, 140 mmol, 5.05 eq) and the mixture was stirred at rt for 24 h. The mixture was concentrated under reduced pressure to a semi-solid. Residual methanol was co-evaporated with toluene (2×50 mL) followed by 1:1 toluene/heptanes (50 mL) to give a white crystalline solid. The solid was triturated with heptanes (50 mL), filtered and dried to give 4.35 g (95%) of 37 as a white solid.

Provenance & Evidence