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

Participants

Reaction Steps

60 mg (0.112 mmol) of (RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester (from example 59.1) in 3 mL of THF were treated with 7 mg (0.168 mmol, 1.5 eq) of NaH (55% in oil) at 0° C. over 40 min. 38 mg (0.224 mmol, 2eq) of bromomethly-benzene were added and the reaction mixture was stirred over night at RT. The solvent was evaporated, the residue was dissolved in 3 mL of CH2Cl2, 1 mL of TFA was added, and the reaction mixture was stirred over night at RT. Evaporation of the solvent and purification of the residue by preparative HPLC (C18 column) yielded 35 mg (60%) of (RS,SR)-2-benzenesulfonyl-N-benzyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide as a white solid, MS: 525 (MH+).

Provenance & Evidence