Pentane → HCID 59452543, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl lithium (1.7 M pentane) (1.05 mL, 1.76 mmol) was added dropwise to a stirring solution of 3a,6a-bis(iodomethyl)-2,5-bis((4-methylphenyl)sulfonyl)octahydropyrrolo[3,4-c]pyrrole (0.50 g, 0.71 mmol) in THF (10 mL) at −78° C. The resulting orange mixture was stirred at −78° C. for 30 minutes. After this time, additional t-Butyl lithium 1.7 M in pentane (1.05 mL, 1.76 mmol) was added to the reaction mixture at −78° C. After 10 minutes of additional stirring at −78° C., the reaction was quenched with the addition of sat. NH4Cl (aq) (10 mL). The mixture was warmed to r.t., diluted with EtOAc (15 mL) and the layers were separated. The aq. layer was then extracted with EtOAc (3×20 mL) and once with CH2Cl2. The combined organic extracts were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give 2,5-bis((4-methylphenyl)sulfonyl)tetrahydro-1H,4H-3a,6a-ethanopyrrolo[3,4-c]pyrrole (0.308 g, 0.690 mmol, 97% yield) as a white crystaline solid. LCMS: m/e=447 (M+H)+. LCMS retention time: 2.39 min. (Column: SunFire C18 5u 4.6×50 mm. Solvent A=90% Water/10% Acetonitrile/0.1% TFA. Solvent B=10% Water/90% Acetonitrile/0.1% TFA. Start % B=0. Final % B=100. Gradient Time=3 min. Flow Rate=4 mL/min.). Structure was verified via single crystal X-ray diffraction. 1H NMR (400 MHz, CHLOROFORM-d) □ ppm 7.67 (4 H, d, J=8.28 Hz), 7.34 (4 H, d, J=8.03 Hz), 3.36 (4 H, d, J=9.79 Hz), 2.73 (4 H, d, J=9.79 Hz), 2.47 (6 H, s), 2.00 (4 H, s).

Provenance & Evidence