(2R,3S,4S)-2-[(4-methoxyphenyl)methyl]pyrrolidine-3,4-diol

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

Procedure: Following the procedure as described in Example 24, except using the material from Example 39 (432 mg, 1.935 mmol), 2-(tert-butoxycarbonylamino)acetic acid (486.1 mg, 2.77 mmol), 1-hydroxy-7-azabenzotriazole (134.0 mg, 0.984 mmol), CH2Cl2 (20 mL), N-methylmorpholine (1.1 mL, 10.01 mmol), and EDC (560.5 mg, 2.92 mmol), 709.1 mg (96%) of the title compound is obtained as a white solid. Purification is done by BIOTAGE® Silica gel chromatography on a 25 g Thompson Single Step silica cartridge using a linear gradient from 100% CH2Cl2 to 100% EtOAc/Hexanes over 12 column volumes. LC/MS (Condition A): ret. T=3.07 min, (M+Na) 403.20.

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

Procedure: To a 500 mL round bottom flask containing solid (2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate (513.3 mg, 1.935 mmol) and a magnetic stir bar is added 2M NH3/MeOH (200 mL, 400 mmol). The resulting light tan solution is capped and stirred at room temp for 5 days. The solvent is removed in vacuo to give the title compound that is used directly “as is” in the next step. LC/MS (Condition A): ret. T=1.42 min, (M+H)+ 224.11. The resulting light tan solution is capped The solvent is removed in vacuo