(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-amine → 1,1,3-Trimethylindan-4-amine

Into an autoclave reaction vessel were charged 104.0 parts by weight of (3R)-1,1,3-trimethyl-4-aminoindane (optical purity of 67.0% ee), 2.55 parts by weight of 5% palladium-carbon (E-type, manufactured by N. E. Chemcat Corporation), and 1.5 parts by weight of toluene, thereby obtaining a mixture. The reaction vessel was sealed and the gas in the reaction vessel was replaced with nitrogen. While the mixture was stirred, into the reaction vessel was charged hydrogen until the internal pressure of hydrogen in the reaction vessel reached 0.5 MPa, and the mixture was stirred at an internal temperature of 60° C. After 1 hour, the gas in the reaction vessel was replaced with nitrogen, and the mixture was stirred at an internal temperature of 150° C. and an internal pressure of 0.1 MPa for 14 hours, thereby obtaining a reaction mixture. The obtained reaction mixture was cooled and filtered using Celite. The obtained solid was washed with 150 parts by weight of toluene. The washing liquid recovered after washing and the filtrate obtained by filtration were combined to obtain a solution of 244.6 parts by weight of 1,1,3-trimethyl-4-aminoindane in toluene. The combined 1,1,3-trimethyl-4-aminoindane had an optical purity of 0.35% ee and a recovery rate of 98.9%. At this time, the filtered catalyst was washed twice with 30 parts by weight of methanol, 30 parts by weight of 10% caustic water, and 30 parts by weight of water twice, thereby recovering 3.84 parts by weight of palladium-carbon, including Celite.