Methanesulfonic Acid → Methanesulfonate

Participants

Reaction Steps

To a solution of (S)-(+)-2-aminopropanamide (1.93 g; 0170 mol) in anhydrousmethanol (60 ml), under stirring and nitrogen, 2.0 g of 4 Å molecular sieves were added and then, in a single portion, NaBH3CN (0.78 g; 0.0124 mol); after 10 minutes, 4 g (0.0155 mol) of 4-(3-(2-fluorophenyl)propyl) oxybenzaldehyde were added, in 20 ml of anhydrous methanol. After 3 hours, the reaction was completed, the mixturewas filtered, the filtrates washed with methanol, the residue was directly flash-chromatographed on silica gel (eluant: CH2Cl2 195: CH3OH 5: 30% NH4OH 0.5) to give a white solid (2.7 g; 53%). The free base thus obtained was treated with a stoichiometric amount of methanesulfonic acid to yield (S)-(+) 2-{4-[3-(2-fluorophenyl)propyl)oxybenzyl}aminopropanamide, methanesulfonate; m.p. 172°-177° C.; [α]25 +10.4 (C=1.06, AcOH).

Provenance & Evidence