1-(1,1-Dimethylethyl) 2-(phenylmethyl) 2-azabicyclo[3.1.0]hexane-1,2-dicarboxylate → HCID 15927972, compound

Participants

Reaction Steps

Compound (5) was dissolved in ethyl acetate (300 ml) and the solution was flushed with argon. Palladium-on-carbon (5%, 3 g) was added and hydrogen was bubbled into the stirred suspension until no starting material remained (2 hours as indicated by TLC). The flask was then flushed with nitrogen and the catalyst was removed by filtration. The catalyst was washed with methanol (3×100 ml) and the combined filtrates were concentrated. The residue was then distilled with a Kuglerohr apparatus at reduced pressure to give 6.6 g (85%) of compound (6) as a light yellow oil: bp=90°-120° C./0.8 mm; 1H NMR (C6D6): δ2.83 (m, 1H), 2.32 (m, 1H), 2.10 (br s, 1H), 1.76 (m, 1H), 1.3-1.65 (m, 3H), 1.36 (s, 9H), 0.85 (t, J=6 Hz) ppm. 13NMR (C6D6) δ172.2 (C=O), 80.1 (quat), 50.1 (quat), 44.3 (CH2), 28.1 (CH2), 27.7 (CH), 16.7 (CH2) ppm.

Provenance & Evidence