Benzyl Alcohol → Benzyl (2r)-2-amino-2-cyclohexylethanoate methanesulfonate

Participants

Reaction Steps

To a suspension of (2R)-2-amino-2-cyclohexylethanoic acid (200 g, 1.27 mol) and benzyl alcohol (276 g, 2.54 mol) in toluene (1600 mL) was added methanesulphonic acid at a rate which did not allow the temperature to reach 100° C. The reaction was stirred for an additional six hours at between 110 and 115° C. The water that was produced was distilled off using a Dean-Stark trap. An additional portion of benzyl alcohol (276 g, 2.54 mol) was added and the mixture was refluxed for a further twelve hours with water distillation. The reaction mixture was then cooled and methyl tert-butyl ether was added to initiate crystallisation. The product was filtered and dried to yield 404 g (92%) of the sub-title compound.

Provenance & Evidence