Aluminium lithium hydride → 1,2,3,3a,8,8a-Hexahydroindeno[1,2-c]pyrrole

Temperature

70 °C

A solution of 3,3a,8,8a-tetrahydro-2H-2-aza-cyclopenta[a]inden-1-one (1.5 g, 8.8 mmol) in THF (44 mL) was cannulated to a solution of LAH in THF (26.4 mL, 1.0 M solution in THF). The resulting solution was stirred for 4 hours at 70° C., then overnight at room temperature. The reaction was quenched via the stepwise addition of H2O (1 mL), aqueous NaOH (1 mL, 2.0 M solution), and H2O (3 mL). The resulting mixture was filtered through celite, the celite washed with warm MeOH (200 mL), and the filtrate concentrated to give the subtitle compound and its regioisomer, which were used without further purification. MS calculated for C11H13N+H: 160, observed: 160.

1. customovernight
2. customat room temperature
3. customThe reaction was quenched via the stepwise addition of H2O (1 mL), aqueous NaOH (1 mL, 2.0 M solution), and H2O (3 mL)
4. filtrationThe resulting mixture was filtered through celite
5. washthe celite washed with warm MeOH (200 mL)
6. concentrationthe filtrate concentrated

ORD record

ord-f120e4fd81fb4519b69e654d82ea6c63

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716324B2