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

HRID 925103

Reaction equation

HRID 925103 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[C@H:4]([CH3:12])[CH2:3]1.[H][H]>[C].[Pd].CC(O)C>[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:12])[CH2:3]1

Participants

5

Reactant 2

HCID 14535936(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 112175411,1,3-Trimethylindan-4-amine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

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), 0.81 part by weight of 5% palladium-carbon (STD-type, manufactured by N. E. Chemcat Corporation), and 12 parts by weight of 2-propanol, thereby obtaining a mixture. The reaction vessel was sealed and the gas in the reaction vessel was replaced with nitrogen. While stirring the mixture at room temperature, into the reaction vessel was charged hydrogen until the internal pressure of hydrogen in the reaction vessel reached 0.5 MPa. After 15 minutes, hydrogen was removed to normal pressure, and the mixture was stirred at an internal temperature of 130° C. and an internal pressure of 0.45 MPa for 7 hours while the inside of the reaction vessel was replaced with hydrogen, thereby obtaining a reaction mixture. The obtained 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 5.55 parts by weight of 1,1,3-trimethyl-4-aminoindane. The obtained 1,1,3-trimethyl-4-aminoindane had an optical purity of 1.2% ee and a recovery rate of 92.5%.

Workup

  1. customobtaining a mixture
  2. customThe reaction vessel was sealed
  3. customhydrogen was removed to normal pressure
  4. stirringthe mixture was stirred at an internal temperature of 130° C.
  5. waitan internal pressure of 0.45 MPa for 7 hours while the inside of the reaction vessel was replaced with hydrogen
  6. customobtaining a reaction mixture
  7. customThe obtained reaction mixture
  8. temperaturewas cooled
  9. filtrationfiltered
  10. washThe obtained solid was washed with 20 parts by weight of 2-propanol
  11. customThe washing liquid recovered
  12. washafter washing
  13. customthe filtrate obtained by filtration
  14. concentrationThe combined mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a20845646eb4a0fa20b237c9745d601
Source dataset
uspto-grants-2016_03
Patent number
US09284260B2

Linked notes

Loading…