Ethanol → tert-butyl N-((4-(aminomethyl)cyclohexyl)methyl)carbamate

HRID 1986865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986865
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16]C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].CCO.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][NH2:16])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 22668023[4-(Tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 2756046tert-butyl N-((4-(aminomethyl)cyclohexyl)methyl)carbamateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of [4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (11.00 g, 32 mmol) dissolved in 2:1 CHCl3:EtOH at room temperature was added 4.0 M HCl/dioxane (16.1 mL). The mixture was stirred at room temperature for 4 h then concentrated in vacuo to provide a crude white solid. The crude material was purified by silica gel chromatography using a gradient elution of 10-50% (2% NH4OH, 18% MeOH, 80% CH2Cl2)/CH2Cl2. The product-containing fractions were combined and concentrated in vacuo to provide (4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester as a white powder 3.62 g, 47%, m/z calculated for C13H26N2O2: 242.4, found: 243.3 (M+H)+.

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customto provide a crude white solid
  3. customThe crude material was purified by silica gel chromatography
  4. washa gradient elution of 10-50% (2% NH4OH, 18% MeOH, 80% CH2Cl2)/CH2Cl2
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fec74920f05143459c2a0a861940e640
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550473B2

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