Methanol → 1-isopropylamino-2,3-dihydro-4-methoxy-1H-indene

HRID 1741419

Reaktionsgleichung

Reaktionsgleichung von HRID 1741419
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.[CH:13]([NH2:16])([CH3:15])[CH3:14].CO>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:13]([NH:16][CH:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 6363IsopropylamineHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 183672411-isopropylamino-2,3-dihydro-4-methoxy-1H-indene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-methoxy-1-indanone (0.71 g) and iso-propylamine (8 ml) in dichloromethane (10 ml) was added 1M solution of titanium(IV) chloride in dichloromethane (11 ml) at -60° C. for 15 minutes. The reaction mixture was stirred for 3 hours at the same temperature. Methanol (15 ml) was added to the reaction mixture. After being stirred for 2 hours at room temperature, the solution was evaporated in vacuo. The residue was partitioned between ethyl acetate and 1N aqueous NaOH solution. The insoluble material was filtered off by zeolite. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 1-isopropylamino-2,3-dihydro-4-methoxy-1H-indene (0.89 g). MS (m/z): 206 (M+ +1) NMR (CDCl3, δ): 7.18 (1H, dd, J=7.8, 7.8 Hz), 6.97 (1H, d, J=7.8 Hz), 6.71 (1H, d, J=7.8 Hz), 4.30 (1H, t, J=6.7 Hz), 3.83 (3H, s), 3.20-2.87 (2H, m), 2.80-2.60 (1H, m), 2.50-2.35 (1H, m), 2.00-1.68 (1H, m), 1.13 (3H, d, J=6.9 Hz), 1.12 (3H, d, J=6.9 Hz)

Aufarbeitung

  1. stirringAfter being stirred for 2 hours at room temperature
  2. customthe solution was evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1N aqueous NaOH solution
  4. filtrationThe insoluble material was filtered off by zeolite
  5. washThe organic layer was washed with brine
  6. customThe dried solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3bf683236f240259165f6681f0fd040
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972965

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