Cyclohexene → 1,1,3-Trimethylindan-4-amine

Temperatur

150 °C

Into a reaction vessel were charged 6.00 parts by weight of (3R)-1,1,3-trimethyl-4-aminoindane (optical purity of 96.5% ee) and 1.60 parts by weight of 5% palladium-carbon (STD-type, manufactured by N. E. Chemcat Corporation), thereby obtaining a mixture. The reaction vessel was sealed, the gas in the reaction vessel was replaced with nitrogen, and then the mixture was stirred at 150° C. to obtain a reaction mixture. While stirring the obtained reaction mixture, 1.40 parts by weight of cyclohexene was added dropwise thereto over 5 hours. Thereafter, the reaction mixture was cooled and filtered. The obtained solid was washed with 20 parts by weight of 2-propanol. The washing liquid recovered after washing and the filtrate obtained by filtration were combined. The combined mixture was concentrated under reduced pressure to obtain 5.63 parts by weight of 1,1,3-trimethyl-4-aminoindane. The obtained 1,1,3-trimethyl-4-aminoindane had an optical purity of 0.29% ee and a recovery rate of 93.8%.

1. customobtaining a mixture
2. customThe reaction vessel was sealed
3. customto obtain a reaction mixture
4. stirringWhile stirring
5. additionwas added dropwise
6. temperatureThereafter, the reaction mixture was cooled
7. filtrationfiltered
8. washThe obtained solid was washed with 20 parts by weight of 2-propanol
9. customThe washing liquid recovered
10. washafter washing
11. customthe filtrate obtained by filtration
12. concentrationThe combined mixture was concentrated under reduced pressure

ORD-Eintrag

ord-3c5b0c32142745efb9b0e9524251feb9

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09284260B2