Sodium hydride → N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamine

HRID 81307

Reaktionsgleichung

Reaktionsgleichung von HRID 81307
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[H-].[Na+].[CH3:25][O:26][CH2:27][CH2:28]Br>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:28][CH2:27][O:26][CH3:25])=[CH:18][CH:17]=1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamine

Produkt 1

HCID 22566171N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamineAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of 29 (4 g, 0.013 mol) in anhydrous THF (150 mL) under nitrogen at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.64 g, 0.016 mol). The mixture was stirred for 15 min then tetrabutylammonium iodide (0.5 g, 0.0013 mol) and 2-bromoethyl methyl ether (2.04 g, 0.015 mol) were added and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate) to provide 64 (3.1 g, 64%). 1H NMR (300 MHz, CDCl3) δ 1.60 (m, 4H), 2.59 (m, 2H), 3.23 (m, 2H), 3.45 (s, 3H), 3.77 (m, 2H), 4.10 (m, 2H), 5.13 (s, 2H), 6.88 (d, 2H), 7.08 (d, 2H), 7.47 (s, 5H).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-98799198116b415281f6166d2dcd170c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846688B2

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