Trifluoroacetic acid → Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Beteiligte Stoffe

Reaktionsschritte

To a solution of (±)-1,1-dimethylethyl cis-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (15.3 g, 43.7 mmole) in DCM (150 mL) at RT was added TFA (50 mL). After 2 h, the reaction solution was concentrated under vacuum and the residue placed under high vacuum for 3 hr. The residue was dissolved in DCM (200 mL) and MP-carbonate resin (175 mmole, 65 g) was added with vigorous stirring at RT. After 4 h, the reaction contents were filtered through a scintered-glass funnel washing with MeOH (100 mL). The filtrate was concentrated under vacuum to give the title compound (10.38 g, 95%) as a white foam: LC-MS (ES) m/e 251 (M+H)+.

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