Aluminium lithium hydride → 3-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester

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Reaction Steps

A solution of 3-allyloxycarbonylamino-N-methoxy-N-methyl-succinamic acid tert-butyl ester, 101, (24.3 g, 76.8 mmol) in THF (60 mL) is treated at −78° C. with lithium aluminum hydride (1 M in THF, 39 mL, 39 mmol) dissolved in ether (200 mL) over 5 minutes. After the consumption of starting material, the solution is cautiously quenched with 1.0 N HCl, washed with 1.0 N HCl (2×100 mL) and brine (1×150 mL). The organic layer is concentrated in vacuo to afford 18.2 g (91% yield) of the desired product as a clear oil. 1H-NMR, (300 MHz, CDCl3): δ 1.45 (s, 9H), 2.75–3.01 (m, 2H), 4.37–4.42 (m, 1H), 4.62–4.64 (d, J=5.4, 2H), 5.25–5.38 (m, 2H), 5.89–6.02 (m, 2H), 9.68 (s, 1H); MS (ESI): m/e=258.11 (M+H).

Provenance & Evidence