Tetrahydrofuran → cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

Participants

Reaction Conditions

Reaction Steps

To a solution of 1 M LAH in THF (800 mL; 0.8 mole; 2.3 eq) at rt was added, portionwise, tetrahydrophthalimide (52.6 g; 0.348 mole; 1 eq). The reaction mixture was stirred at 60° C. for 16 hours, then cooled to RT and quenched carefully with sequential addition of 30 mL of water, 30 mL of THF, 15% aqueous KOH (30 mL), and water (100 mL). The mixture was diluted with 135 mL of ether, stirred at RT for 1 hour, and filtered through a pad of diatomaceous earth on a 600 mL fritted glass filter funnel, washing the pad with 400 mL of DCM. The filtrate was concentrated in vacuo to yield (3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-isoindole as an oil, which was used directly in the next reaction as is.

Provenance & Evidence