Diisopropylethylamine → (2R)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine

HRID 1014331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014331
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[NH:9][CH2:8][CH2:7]2.[CH3:16][N:17]([CH3:23])[C@@H:18]([C:20](O)=[O:21])[CH3:19].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C)C=O>[CH3:16][N:17]([CH3:23])[C@H:18]([CH3:19])[C:20]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=2)[CH2:7][CH2:8]1)=[O:21]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151045(2R)-2-(dimethylamino)propanoic acidHCID 2724699PyBOPHCID 673167385-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrochloride

Produkt 1

HCID 59441930(2R)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamineAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride (2 g, 8.67 mmol) in N,N-dimethylformamide (100 mL) was added N,N-dimethyl-D-alanine (1.524 g, 13.01 mmol), PyBOP (13.54 g, 26.0 mmol), and DIPEA (15.14 mL, 87 mmol). After stirring overnight at rt, the solvent was removed and the residue was suspended in dichloromethane (150 mL), washed with water (100 mL), concentrated on the rotovap, and purified by column chromatography (DCM to 5% MeOH/DCM) to provide 1-[(2R)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine (2.2 g, 86%). ESIMS (M+H)+=294.

Aufarbeitung

  1. customthe solvent was removed
  2. washwashed with water (100 mL)
  3. concentrationconcentrated on the rotovap
  4. custompurified by column chromatography (DCM to 5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c1ac11735ac44fdd933adc16ff7ffc94
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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