N,N,N',N'-Tetramethylazodicarboxamide → N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine

HRID 10501

Reaktionsgleichung

Reaktionsgleichung von HRID 10501
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22]O)([CH3:16])([CH3:15])[CH3:14].N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:13]([O:17][C:18]([NH:19][CH2:20][CH2:21][CH2:22][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[Cl:1])=[O:24])([CH3:16])([CH3:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 219799331-Chloroisoquinolin-5-ol

Produkt 1

HCID 21979957N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 1-chloro-5-hydroxyisoquinoline (539 mg, synthesized according to the method described in a reference (Georgian, V. et al., J. Org. Chem., 27, 4571 (1962))), (3-hydroxypropyl)carbamic acid tert-butyl ester (1.58 g, Tokyo Kasei Kogyo) and 1,1′-azobis(N,N-dimethylformamide) (1.55 g) in tetrahydrofuran (8 ml) was added with tri(n-butyl)phosphine (2.24 ml) with ice cooling and stirred at room temperature for 24 hours. The deposited solid was removed by filtration, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (860 mg) as white powdery solid.

Aufarbeitung

  1. customsynthesized
  2. customThe deposited solid was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThen, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-881ac3f56ed04e33b46fda327ae9d93f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094789B2

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