Triethylamine → (RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester

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Reaction Steps

To 950 mg (2.18 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide (from example 56) in 10 mL of CH2Cl2 at RT were added 0.60 mL (4.36 mmol, 2 eq) of Et3N, 27 mg (0.22 mmol, 0.1 eq) of DMAP and 571 mg (2.62 mmol, 1.2 eq) of carbonic acid di-tert-butyl ester. The reaction mixture was stirred at RT for 2 hours and extracted with 1M HCl. The organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography afforded 682 mg (59%) of (RS,SR)-2-(benzenesulfonyl-fluoro-methylcarbamoyl-methyl)-6-chloro-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester as white solid, MS: 552 (MNH4+).

Provenance & Evidence