[(3S,4R)-4-(hydroxymethyl)pyrrolidin-3-yl]methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (cis)-3,4-Pyrrolidinediyldimethanol (970 mg, 7.4 mmol) was dissolved in a mixture of MeOH (20 mL) and water (7 mL) and cooled to 0° C. Na2CO3 (1.96 g, 19 mmol) was added followed by benzyl chloroformate (1.15 mL, 8.1 mmol) and the resulting solution was stirred for 4 hours, maintaining the temperature at 0° C. The reaction was concentrated under reduced pressure to remove most of the methanol, and the remaining aqueous solution was extracted twice with EtOAc. The combined organics were washed with brine and dried over sodium sulfate before being concentrated in vacuo. RP-HPLC yielded phenylmethyl (cis)-3,4-bis(hydroxymethyl)-1-pyrrolidinecarboxylate (450 mg, 22%, 1.7 mmol). LCMS: (M+H)+: 266.1. maintaining the temperature at 0° C The reaction was concentrated under reduced pressure to remove most of the methanol the remaining aqueous solution was extracted twice with EtOAc The combined organics were washed with brine dried over sodium sulfate before being concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of crude [(cis)-1-(phenylmethyl)-3,4-pyrrolidinediyl]dimethanol (2.5 g) in MeOH (50 mL) was added conc HCl (0.2 mL) followed by Pearlmans catalyst (700 mg). The resulting suspension was hydrogenated for 48 hours at 50 psi on a Parr shaker, after which time a further 700 mg of the catalyst was added. Hydrogenation for another 72 hours at 50 psi resulted in completion of the reaction. Removal of the catalyst by filtration and evaporation of the solvents under reduced pressure yielded (cis)-3,4-pyrrolidinediyldimethanol (970 mg, 7.4 mmol). LCMS: (M+H)+: Not detected. Hydrogenation for another 72 hours at 50 psi resulted in completion of the reaction Removal of the catalyst by filtration and evaporation of the solvents under reduced pressure