Hydrazine → HCID 69336447, compound

Participants

Reaction Steps

To the starting material, 1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (0.560 g, 1.34 mmol) (Intermediate 20) was added ethanol (10 mL) and hydrazine (35% in H2O, 0.483 mL, 5.36 mmol). The reaction was heated to reflux, and although within a few minutes a solid precipitated that impeded stirring, the reaction was heated for a total of 80 minutes. The solvent was removed at reduced pressure and the residue partitioned between 1N NaOH solution and methylene chloride. The organics were washed with a saturated solution of citric acid two times and the methylene chloride discarded. The aqueous layer was basified with sodium bicarbonate and extracted with methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give 1-aminomethyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester as an oil (0.268 g, 69% yield).

Provenance & Evidence