4-Methylmorpholine → Tert-butyl 3-[(2-acetylhydrazino)carbonyl]pyrrolidine-1-carboxylate

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Reaction Steps

Isobutyl chloroformate (152 μL, 1.16 mmol) was added to a stirred solution of 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (237 mg, 1.10 mmol) and 4-methylmorpholine (182 μL, 1.65 mmol) in THF (5.50 mL) at −78° C. After 15 min, added acetic hydrazide (2.0 mg, 1.10 mmol), and the resulting mixture was warmed slowly to rt. After 1 h, the reaction mixture was quenched with 0.5 M HCl and extracted with EtOAc. The combined organics were dried (sodium sulfate) and concentrated in vacuo to afford the title compound i-8a. m/z (ES) 272 (MH)+.

Provenance & Evidence