Dimethyl Sulfide → Ethyl N-(2-{(tert-butoxycarbonyl)[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)glycinate

Participants

Reaction Steps

To a solution of tert-Butyl [(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]prop-2-en-1-ylcarbamate (45 mg, 0.14 mmol) in MeOH (5 mL) was bubbled ozone until the solution turned blue. Excess ozone was removed by bubbling nitrogen through. To the reaction was then added DMS (0.50 ml, 6.8 mmol), and it was allowed to warm to RT. The solvent was removed under reduced pressure, and the resulting material was further treated with ethyl aminoacetate hydrochloride (13 mg, 0.090 mmol) and sodium cyanoborohydride (6.0 mg, 0.090 mmol). When LC showed the reaction was done, the reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, and purified by MPLC to deliver the title product. LC-MS (IE, m/z): 420 [M+1]+.

Provenance & Evidence