Hydrazine hydrate (1:1) → HCID 86731684, compound

Participants

Reaction Steps

To a solution of tert-butyl {1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]cyclopropyl}carbamate (80.0 g, 253 mmol) in methanol (1600 mL) was added hydrazine hydrate (80% solution in water, 15.9 g, 320 mmol). The reaction mixture was heated to reflux. After 4 hours, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was washed with DCM (3×500 mL) and then the combined organic layers were concentrated under reduced pressure. This residue was dissolved in diethyl ether (1000 mL) and diluted with oxalic acid dihydrate (solution in ethanol, 35.2 g, 279 mmol), which was added dropwise. After 1 hour, the precipitated solids were collected by filtration, washed with diethyl ether (4×200 mL), and dried to give tert-butyl [1-(aminomethyl)cyclopropyl]carbamate oxalate salt. MS ESI calc'd. for C9H19N2O2 [M+H]+ 187. found 187. 1H NMR (400 MHz, D2O) δ 2.98 (s, 2H), 1.36-1.30 (m, 9H), 0.81 (s, 4H).

Provenance & Evidence