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

Participants

Reaction Steps

To a flask containing 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (for a preparation see Example 135(e)) (1 g; 2.74 mmol) was added 100 mL of TFA/DCM (50%). The reaction mixture was stirred for 1 h and then concentrated. The crude product was made basic by the addition of 6N NaOH and extracted into 10% MeOH/DCM (2×50 mL). The organic fractions were dried with anhydrous sodium sulfate, filtered and concentrated to obtain the product as a clear oil (607 mg; 84%).

Provenance & Evidence