Thioanisole → 952494-13-2

Participants

Reaction Conditions

Reaction Steps

To 2-(3,4-dimethoxy-benzyl)-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid (9.6 g, 26 mmol), prepared in manner analogous to 2-cyclopropyl-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid, is added thioanisole (36 mL, 304 mmol) and trifluoroacetic acid (360 mL). The resulting solution is heated to 70° C. for 13 h. The reaction is then cooled to room temperature and concentrated in vacuo to near dryness. The resulting purple oil is purified via silica gel flash chromatography (dichloromethane-methanol, 1:0 to 9:1, with 0.5% acetic acid) to furnish 3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid as an off-white foam; MS (ESI) m/z 220.0 (M+H).

Provenance & Evidence