Trifluoroacetic acid → (+/-)-Phenylmethyl {[trans-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Participants

Reaction Steps

To a stirred solution of (±)-1,1-dimethylethyl trans-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (4.44 g, 12.7 mmole) in DCM (75 mL) was added TFA (25 mL). After stirring for 2 h, the reaction contents were concentrated under vacuum and the residue dissolved in DCM (150 mL). MP-carbonate resin (18.8 g, 50.8 mmole) was added and the reaction contents were stirred vigorously overnight. The reaction contents were filtered through a scinter-glass funnel and the resin washed with MeOH. The filtrate was concentrated and dried under vacuum to give an off-white foam: LC-MS (ES) m/e 251 (M+H)+.

Provenance & Evidence