Acetic Acid → Ammonia

Participants

Reaction Steps

To (S)-2-Methyl-propane-2-sulfinic acid [(R)-1-[(1S,5R)-8-(2-amino-acetyl)-bicyclo[3.2.1]oct-3-yl]-2-(2,4,5-trifluoro-phenyl)-ethyl]-amide (150 mg, 0.33 mmol) in methanol (3 mL) is added acetic acid until to have pH 5-5.5. After addition of acetone (124 uL, 1.68 mmol), the reaction is stirred at rt during 1 h and sodium cyanoborohydride (43 mg, 0.67 mmol) is added before stirring at rt during 16 h. The reaction is quenched with ethylacetate and an aqueous saturated NaHCO3 solution, the organic phase is dried and evaporated to afford the crude compound before purification onto a SCX-2 cartridge (5 g, DCM/MeOH 1:1, then 2N NH3 in MeOH) to yield the title compound.

Provenance & Evidence