1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate → Phenylmethyl {[(3R,4R)-4-hydroxy-3-piperidinyl]methyl}carbamate

Participants

Reaction Steps

To a flask containing 1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E2)(500 mg; 1.37 mmol) was added 20 mL of TFA/DCM (50%). The reaction mixture was stirred for 1 h and then concentrated. The crude product was taken up in chloroform, treated with 500 mg of MP-carbonate resin (2.9 mmol/g) and stirred overnight. After filtration and concentration the product was obtained as its free base (370 mg; 100%).

Provenance & Evidence