Methane → HCID 58092727, compound

Participants

Reaction Steps

Trimethylaluminum in toluene (2 M, 3.23 mL) was added dropwise to a mixture of ammonium chloride (0.346 g, 6.47 mmol) in toluene (3.2 mL) at 0° C. under an argon atm., with the formation of methane gas. The RM was then allowed to warm to rt, and stirred at rt for a further 15 min. before (2S,3R)-3-methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester (prepared as described in Tetr. Lett. 1997, 38 (1), 85-88; 1.6 g, 6.47 mmol) was slowly added. The RM was stirred at it for 56 h, 1 M HCl was then added with cooling and the RM washed 3× with DCM. The aqueous phase was basified with Na2CO3, extracted 3× with DCM and the combined organic layers dried over Na2SO4. Evaporation gave the title compound as a yellowish oil. MS: M+H=233.2. HPLC: tR 3.17 min (method D). 1H-NMR (d6-DMSO, 600 MHz): 7.37-7.33 (m, 2H), 7.30 (t, 2H), 7.25 (s, br,1H), 7.21 (t, 1H), 7.12 (s, br,1H), 3.55 (q, 1H), 3.40 (d, 1H), 2.71 (t, 1H), 2.28-2.22 (m, 1H), 2.21-2.16 (m, 1H), 1.71 (qt, 1H), 1.38-1.31 (m, 1H), 1.21 (d, 3H), 0.90 (d, 3H).

Provenance & Evidence