Sodium Sulfate → (3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanol

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Reaction Conditions

Reaction Steps

Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate (37.2 g, 136.3 mmol) was dissolved in dry THF (400 ml). This solution was added dropwise at 0° C. to a suspension of LiAlH4 (20.7 g, 545.3 mmol) in dry THF (200 ml). The resulting brown suspension was heated to 60° C. under nitrogen atmosphere for 36 h. The mixture was then cooled to 0° C. and quenched carefully with sat. NH4Cl. A grey solid formed and more THF was added to allow adequate stirring. Solid Na2SO4 was added to the mixture which was stirred at r.t. for 30 min. The mixture was then filtered through celite to give a pale yellow solution. This was concentrated in vacuo to give the title compound as an orange oil (14.1 g, 51%). m/z 204 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 2.25 (2H, d), 2.85 (2H, d), 3.20 (2H, t), 3.55 (2H, s), 4.35 (1H, t), 7.20-7.40 (5H, m).

Provenance & Evidence