1-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclo-penta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide → 1-[(2,2-Difluorocyclopropyl)methyl]-3-methyl-5-(octahydrocyclopenta[c]-pyrrol-5-yl)-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

Participants

Reaction Steps

1-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclo-penta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (24-2, 100 mg, 0.26 mmol, 1.0 equiv) was added to anhydrous methanol (2.6 mL). To this solution was added 10% palladium(0) on carbon (55.7 mg, 0.052 mmol, 0.2 equiv) to give a black suspension. The reaction flask was evacuated and back-filled with hydrogen from a balloon. This process was repeated an additional 2 times. The resulting mixture was allowed to stir under an atmosphere of H2 for 30 min. Following this duration, LCMS showed complete consumption of starting material. The reaction contents were filtered through Celite, washed with DCM and concentrated to give 25-1 as an off-white solid. The crude material was carried forward without additional purification.

Provenance & Evidence