1-Phenethylamine, (-)- → HCID 10685833, compound

Participants

Reaction Steps

A mixture of (3R,4S,5S), and (3S,4R,5R), -N-tert-Butyloxycarbonyl-4-hydroxy-piperidine-3,5-dicarboxylic acid 3-methyl ester (96% ee) (78 g, 0.26 mol) is dissolved in MeOH (500 mL) and (S)-(−)1-phenylethylamine (33 mL, 0.26 mol) at room temperature is added. The mixture is stirred for 30 min at room temperature and concentrated under reduced pressure to provide a salt as a colorless amorphous. The resulting residue is dissolved in CH3CN (1.3 L) at 70° C. and stirred vigorously at room temperature for 20 h. A white crystalline salt is collected by filtration, washed with Et2O. After repeating the same recrystallization procedure (dissolution in CH3CN and stirring at room temperature) two or three times the resulting salt is dissolved in water, acidified to pH 3 with 5N and 1N HCl, and extracted with AcOEt. The combined organic phases are dried over Na2SO4. Concentration under reduced pressure gives enantiomeric pure (3R,4S,5S)-starting material-G as a white solid: ES-MS: M+H=304: CtRet=2.37 min. chiral HPLC: >99.9% ee, AD-H, 7.5% i-PrOH/Hexane/0.1% TFA, flow 0.75 mL/min, 210 nm, tRet=24 min

Provenance & Evidence