(2S,4R)-4-hydroxypyrrolidine-2-carboxamide

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

Procedure: To a solution of (2S,4R)-2-aminocarbonyl4-hydroxypyrrolidine (1.40 g) in acetic acid (12.4 ml) and water (6.8 ml), 37% aqueous formaldehyde solution (1.09 g) and platinum oxide (33 mg) were added, and the mixture was vigorously stirred at room temperature for 16 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered, followed by removal of the solvent. The residue was dissolved in isopropanol, and magnesium sulfate and potassium carbonate were added thereto. The resultant mixture was stirred at room temperature for 1 hour and filtered. After removal of the solvent, the residue was purified by silica gel column chromatography to give (2S,4R)-1-methyl-2-aminocarbonyl-4-hydroxypyrrolidine. The reaction mixture was filtered followed by removal of the solvent The residue was dissolved in isopropanol magnesium sulfate and potassium carbonate were added filtered After removal of the solvent the residue was purified by silica gel column chromatography

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

Procedure: A solution of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid benzyl ester (1 g) in 880 ammonia (5 ml) was stirred for 18 h then evaporated and triturated with Et2O to give the title compound as a white solid. 1H-NMR (d6-DMSO, 400 MHz): 9.15 (s, br, 1H), 8.04 (s, 1H), 7.63 (s, 1H), 5.56 (s, 1H), 4.40 (s, 1H), 4.27-4.16 (m, 1H), 3.27 (d, 1H), 3.02 (d, 1H), 2.33 -2.19 (m, 1H), 1.89-1.76 (m, 1H). then evaporated triturated with Et2O

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

Procedure: A solution of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid benzyl ester (1 g) in 880 ammonia (5 ml) is stirred for 18 hours then evaporated and triturated with diethyl ether to give the title compound as a white solid. 1H nmr (d6-DMSO, 400 MHz) 9.15 (s, br, 1H), 8.04 (s, 1H), 7.63 (s, 1H), 5.56 (s, 1H), 4.40 (s, 1H), 4.27-4.16 (m, 1H), 3.27 (d, J=7 Hz, 1H), 3.02 (d, J=7 Hz, 1H), 2.33-2.19 (m, 1H), 1.89-1.76 (m, 1H). then evaporated triturated with diethyl ether