Diethyl Ether → cis-Octahydroisoindole

Temperature

0 °C

Cis-4-cyclohexene-1,2-dicarboximide (10.9 g) was hydrogenated over 10% palladium on carbon (1 g) in absolute ethanol (420 ml) at 50 psi for 10 minutes. The mixture was filtered then evaporated to give cis-cyclohexane-1,2-dicarboximide (10.6 g). To anhydrous diethyl ether (200 ml) was cannulated under nitrogen a 1M diethyl ether solution (200 ml) of lithium aluminium hydride. To the foregoing solution, under reflux, was added cis-cyclohexane-1,2-dicarboximide (10.6 g) portionwise over 10 minutes. The reaction mixture was heated to reflux for 3 hours. After cooling to 0° C., water (7 ml) was added followed by 4N sodium hydroxide (7.6 ml) and water (23 ml). The white suspension was stirred whilst warming to room temperature. The solid was removed by filtration then the filtrate dried (sodium sulphate) and evaporated to give a cream oil.

1. temperatureTo the foregoing solution, under reflux
2. temperatureThe reaction mixture was heated
3. temperatureto reflux for 3 hours
4. temperaturewhilst warming to room temperature
5. customThe solid was removed by filtration
6. dry with materialthe filtrate dried (sodium sulphate)
7. customevaporated
8. customto give a cream oil

ORD record

ord-6da0a4cd95cd436fb3bebd056b0cd0b4

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05618812