Hydroxyamine hydrochloride → 3,6-Diaza-bicyclo(3.2.0)heptane-6-carboxylic acid tert-butyl ester

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Reaction Steps

Allyl-(2-hydroxyimino-ethyl)-carbamic acid benzyl ester. To a 1 L round-bottomed flask, were added allyl-(2-oxo-ethyl)-carbamic acid benzyl ester (45.2 g, 193.8 mmol) and hydroxylamine hydrochloride (17.5 g, 251.9 mmol) in acetonitrile (260 mL). To the resulting mixture was added a solution of sodium acetate trihydrate (29.5 g, 217 mmol) in H2O (130 mL). The reaction mixture was stirred at room temperature under nitrogen(g) overnight. The mixture was concentrated under reduced pressure and the resulting residue was extracted with ethyl acetate (2×130 mL). The combined organics were washed with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (46.5 g, 97%). 1H-NMR (CDCl3, 400 MHz): 7.32 (m, 5H), 6.72 (m, 1H), 5.77 (bs, 1H), 5.16 (m, 4H), 4.19 (m, 1H), 3.95 (m, 3H). MS (electrospray): exact mass calculated for C13H16N2O3, 248.12; m/z found, 249.1 [M+H]+.

Provenance & Evidence