(2R)-N-phenylpyrrolidine-2-carboxamide

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

Procedure: To a solution of D-Proline anilide (1.15 g, 6.0 mmol) in 20 mL of THF at 0° C. was added a 1 M solution of lithium aluminum hydride (14 mL, 14 mmol) in THF. The resulting solution was stirred at 0° C. for 11 hours. The reaction was carefully quenched with a saturated solution of Na2SO4 and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as an oil. The oil was purified by silica gel chromatography with 3% CH3OH/CH2Cl2 and 1% triethyl amine to give the title compound as a yellow oil (0.029 g, 63%). ES (+) MS m/e=177 (M+H) The reaction was carefully quenched with a saturated solution of Na2SO4 extracted with EtOAc The organic layer was dried over sodium sulfate filtered concentrated under reduced pressure

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

Procedure: 201 mg (1.05 mmol) of EDCl was added to 5 ml of THF solution of 100 mg (0.526 mmol) of Boc-Pro-OH (manufactured by Tokyo Chemical Industry Co., Ltd), and 113 mg (0.526 mmol) of H-D-Pro-NHPh (manufactured by Tokyo Chemical Industry Co., Ltd), followed by stirring for 6 hours at room temperature. After a reaction mixture was concentrated under reduced pressure, the concentrate was extracted by adding water and ethyl acetate. After an organic layer was washed sequentially with a diluted hydrochloric acid, an aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio)), thereby obtaining 160 mg of the product with a yield of 73.6%. After a reaction mixture was concentrated under reduced pressure the concentrate was extracted by adding water and ethyl acetate After an organic layer was washed sequentially with a diluted hydrochloric acid an aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure obtaining crude amide The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio))