cis-Octahydroisoindole → HCID 86650779, compound

cis-Octahydro-1H-isoindole (1.81 g, 14.5 mmol), which is the compound described in Tetrahedron, 55 (1999) 9439-9454, was dissolved in 1N hydrochloric acid (16 ml), and the mixture was stirred under ice-cooling, sodium nitrite (6.22 g, 90.1 mmol) dissolved in water (20 ml) was gradually added, and the mixture was stirred at the same temperature for 3 hr. The reaction mixture was extracted with diethyl ether, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. Me insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (1.22 g, yield 55%) as a bistered oil.

1. temperaturecooling
2. additionwas gradually added
3. stirringthe mixture was stirred at the same temperature for 3 hr
4. extractionThe reaction mixture was extracted with diethyl ether
5. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationMe insoluble material was filtered off
8. concentrationthe solution was concentrated under reduced pressure

ORD record

ord-6e71afdba908458cbe7351868ff05cd6

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2