(2S)-2-amino-1-pyrrolidin-1-ylbutan-1-one

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

Procedure: A mixture of sodium triacetoxyborohydride (279 mg, 1.315 mmol) and (S)-2-amino-1-(pyrrolidin-1-yl)butan-1-one (123 mg, 0.789 mmol) in DCE (2 mL) was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C. A solution of 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (200 mg, 0.657 mmol) in DCE (2 mL) was added, followed by acetic acid (1 drop). The reaction was stirred at 0° C. for 30 min and then at room temperature for 3 h. Purification by silica column chromatography (EtOAc/DCM, 0-10%) afforded the title compound as a yellow oil (83mg, 28.4%). [M+H] calc'd for C23H32N4O5, 445; found, 445.5. The reaction mixture was cooled to 0° C The reaction was stirred at 0° C. for 30 min at room temperature for 3 h Purification by silica column chromatography (EtOAc/DCM, 0-10%)

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

Procedure: A mixture of sodium triacetoxyborohydride (279 mg, 1.315 mmol) and (S)-2-amino-1-(pyrrolidin-1-yl)butan-1-one (123 mg, 0.789 mmol) in DCE (2 mL) was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C. A solution of 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (200 mg, 0.657 mmol) in DCE (2 mL) was added, followed by acetic acid (1 drop). The reaction was stirred at 0° C. for 30 min and then at room temperature for 3 h. Purification by silica column chromatography (EtOAc/DCM, 0-10%) afforded the title compound as a yellow oil (83 mg, 28.4%). [M+H] calc'd for C23H32N4O5, 445; found, 445.5. The reaction mixture was cooled to 0° C The reaction was stirred at 0° C. for 30 min at room temperature for 3 h Purification by silica column chromatography (EtOAc/DCM, 0-10%)

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

Procedure: Phenylmethyl [(1S)-1-(1-pyrrolidinylcarbonyl)propyl]carbamate (J. Med. Chem., 1991, 34, 3149-58) was dissolved in methanol (20 mL) (559 mg, 1.9 mmol). Pd(OH)2 (140 mg) was added, and the resulting suspension was stirred under a hydrogen balloon until the deprotection was complete. Filtration of the catalyst and evaporation of the solvent yielded [(1S)-1-(1-pyrrolidinylcarbonyl)propyl]amine (291 mg, 97%). Filtration of the catalyst and evaporation of the solvent