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

Temperatur

60 °C

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).

1. temperatureThe mixture was then cooled to 0° C.
2. customquenched carefully with sat. NH4Cl
3. customA grey solid formed
4. filtrationThe mixture was then filtered through celite
5. customto give a pale yellow solution
6. concentrationThis was concentrated in vacuo

ORD-Eintrag

ord-d8ec6f293cd34bc59d8277ace0083a8d

Quelldatensatz

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07932246B2