Borane;tetrahydrofuran → HCID 11168903, compound

Participants

Reaction Steps

To 61 mg (0.107 mmol) of (RS,SR)-3-({[2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-acetyl]-methyl-amino}-methyl)-benzoic acid (from example 73) in 3 mL of THF at 0° C., 160 μL (0.107 mmol, 1 eq) of BH3.THF (1M in THF) were added, and the reaction mixture stirred for an additional hour, and then partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with EtOAc/heptane 2:1 yielded 50 mg (84%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-(3-hydroxymethyl-benzyl)-N-methyl-acetamide as a white solid, MS: 555 (M).

Provenance & Evidence