HCID 86638798, compound → HCID 59180175, compound

Participants

Reaction Steps

The title compound was synthesized from SEM-protected ethyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (ethyl 6-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) (0.5 g, 2.79 mmol) and methylmagnesium bromide (4.85 mL, 6.8 mmol, 1.4 M in toluene, 2.2 equiv) according to General Procedure 3 to give ethyl 6-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1,4-dihydrocyclopenta[b]pyrrole-2-carboxylate. The ethyl 6-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1,4-dihydrocyclopenta[b]pyrrole-2-carboxylate was then deprotected according to General Procedure 10.3 to provide ethyl 6-methyl-1,4-dihydrocyclopenta[b]pyrrole-2-carboxylate, which was subjected to hydrogenation according to General Procedure 6. The crude product was purified by preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 60% methanol and increasing to 100% over 7 minutes) afforded the title compound (20.8 mg, 47%). LCMS m/e 216 (M+Na). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.24 (d, J=6.83 Hz, 3H), 1.35 (t, J=7.11 Hz, 3H), 1.90-2.02 (m, 1H), 2.50-2.70 (m, 3H), 3.08-3.20 (m, J=6.92, 6.92, 6.92, 6.92, 6.77 Hz, 1H), 4.30 (qd, J=7.12, 1.39 Hz, 2H), 6.65 (d, J=1.64 Hz, 1H), 8.72 (br. s, 1H).

Provenance & Evidence