Sodium Sulfide → HCID 67253153, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-7-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one (10 g, 24.7 mmol) and TMSI (50 g, 250 mmol) was heated to 80° C. for 2 hours. The mixture was cooled to 0° C. in an ice-water bath. To the mixture, was added 5% aqueous sodium sulfide solution. The mixture was stirred at room temperature until all solid dissolved. The mixture was extracted with methylene chloride. The organic layer was washed with brine. The solvent was removed in vacuo to give a foam. The crude mixture was purified by column chromatography (silica gel. MeOH/CH2Cl2) to give (S)-7-amino-2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one (6 g), which was used in the next step without further purification.

Provenance & Evidence