HCID 54064258, compound → HCID 20672417, compound

Participants

Reaction Steps

A dry flask was charged with N-Methyl-N-methoxy-(R)-2-cyclobutylpropionamide (2.62 grams, 15.4 mmol, from Step D). The vessel was purged with nitrogen and 40 mL THF was added. The mixture was cooled to −10 C and a solution of phenyllithium (30 mL, 1.8 M, 53.9 mmol) was added. The solution was stirred for 1 h at −10 C then the reaction was quenched with sat'd ammonium chloride. The mixture was extracted with ethyl acetate and the organic portion was dried over sodium sulfate and concentrated. Flash chromatography (99/1 hexane/ethyl acetate) afforded 2.06 grams (70%) of the title compound. 1H NMR 400 MHz, CDCl3). δ 1.13 (d, 3H), 1.59-1.7 (m, 1H), 1.73-2.0 (m, 5H), 2.05-2.15 (m, 1H), 2.6-2.7 (m, 1H), 3.43-3.53 (m, 1H), 7.44-7.5 (t, 2H), 7.55-7.6 (m, 1H), 7.97-8.0 (d, 2H).

Provenance & Evidence