Oxalyl chloride → Tert-butyl 2-(4-fluorobenzyl)-2-[(8-benzyloxy-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)carbonyl]hydrazinecarboxylate

Participants

Reaction Steps

To a cold (0° C.) solution of tert-butyl 2-(4-fluorobenzyl)hydrazinecarboxylate (7.30 g, 30.37 mmol; see Fassler et al., J. Med Chem. 1996, 3203) and diisopropylethylamine (10.70 g, 82.82 mmol) in dichloromethane (200 mL), a solution of 8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carbonyl chloride (8.80 g, 27.61 mmol; derived from treatment of the corresponding acid with oxalyl chloride in dichloromethane in the presence of catalytic amount of DMF at room temperature) in dichloromethane was added. The resultant mixture was stirred at room temperature overnight. The resultant mixture was washed with aqueous ammonium chloride, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the titled amide. This was used with no further purification.

Provenance & Evidence