Methanol → 1-Methyl-D-tryptophan methyl ester hydrochloride

Participants

Reaction Steps

Thionyl chloride (1.3 mL, 18.4 mmol) was added dropwise to a suspension of 1-methyl-D-tryptophan (2.0 g, 9.2 mmol) in MeOH (30 mL) at 0° C. under a nitrogen blanket. The resulting mixture was warmed slowly to room temperature and stirred for a total of 20 hours. The solvent was removed under reduced pressure and triturated with Et2O (20 mL). The solids were collected by vacuum filtration, then dried in a vacuum oven at 60° C. for 3 days to provide Intermediate 1 as an off-white powder, which was used without further purification (2.4 g, 96%): TLC Rf (1:2 EtOAc/CHCl3)=0.22.

Provenance & Evidence