Hydrazine hydrate (1:1) → tert-butyl N-(1-amino-4-methanesulfonylbutan-2-yl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfonyl)butan-2-yl]carbamate (25 g, 63 mmol) in ethanol (500 mL) was added dropwise hydrazine hydrate (32 g, 0.63 mol) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes and then heated to reflux. After 2 hours, the reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel to give tert-butyl [1-amino-4-(methylsulfonyl)butan-2-yl]carbamate. MS ESI calc'd. for C10H23N2O4S [M+H]+ 267. found 267. 1H NMR (300 MHz, CD3OD) δ 3.59-3.54 (m, 1H), 3.29-3.09 (m, 2H), 2.96 (s, 3H), 2.71-2.56 (m, 2H), 2.08-1.76 (m, 2H), 1.45 (s, 9H).

Provenance & Evidence