Red-Al → 4-(3,3,7-Trimethylindolin-6-yl)morpholine

HRID 1618613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618613
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[C:6]([CH3:17])[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][C:3]1=O.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[C:6]([CH3:17])[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 16684438Red-AlHCID 672854763,3,7-Trimethyl-6-morpholinoindolin-2-one

Produkt 1

HCID 672846634-(3,3,7-Trimethylindolin-6-yl)morpholineAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 3,3,7-trimethyl-6-morpholinoindolin-2-one (45.7 mg, 0.176 mmol) in toluene (10 mL) at 80° C. under N2, Red-Al (0.18 mL, 3M, 0.53 mmol) was added dropwise. The resultant mixture was stirred at 80° C. for 2 h. The mixture was cooled to rt and quenched with NaOH (2 mL, 3N). The mixture was diluted with EtOAc and washed with water and brine, dried and concentrated. Purification of the residue by flash chromatography over silica gel, using 40% EtOAc in hexane, gave 4-(3,3,7-trimethylindolin-6-yl)morpholine (33.1 mg, 76%): 1H-NMR (DMSO-d6) δ 6.74 (1H, d, J=8.0 Hz), 6.29 (1H, d, J=8.0 Hz), 5.11 (1H, s), 3.69 (4H, s), 3.16 (2H, s), 2.72 (4H, s), 1.96 (3H, s), 1.18 (6H, s). Mass Spectrum (ESI) m/e=247.1 (M+1).

Aufarbeitung

  1. customquenched with NaOH (2 mL, 3N)
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0d223cabc6c04c0bb94ccfbbe3167366
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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