1-Phenethylamine, (-)- → rel-1-(1,1-Dimethylethyl) 3-methyl (3R,5S)-1,3,5-piperidinetricarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (3R*,5S*)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid (6.16 g), (S)-(−)-1-phenylethylamine (2.60 g) and ethanol (24 ml) was dissolved by heating to 70° C. and recrystallization was conducted. The precipitated crystals were collected by filtration, dissolved again in ethanol (7 ml) and recrystallization was carried out. The precipitated crystals were collected by filtration, and suspended in water. The suspension was acidified with saturated aqueous potassium hydrogen sulfate solution, and the mixture was extracted three times with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object compound (915 mg) as a powder.

Provenance & Evidence