Sodium Cyanide → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide

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Reaction Conditions

Reaction Steps

To 400 mg (0.92 mmol) of (RS,SR)-benzenesulfonyl-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-fluoro-acetic acid methyl ester (from example 12) in a sealed tube were added 20 mL of methylamine (33% wt. solution in EtOH) and 13 mg (0.27 mmol, 0.3 eq) of sodium cyanide. The reaction mixture was stirred at 90° C. for 2 hours, and the solvent was evaporated. Column chromatography on silica gel with EtOAc yielded 340 mg (86%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide as a white solid, MS: 435 (MH+).

Provenance & Evidence