Benzylamine → 3-Benzyl-8-oxa-3-azabicyclo[3.2.1]octane

HRID 1375051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375051
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH2:24][CH:25]1[CH2:29][CH2:28][CH:27]([CH2:30]O)[O:26]1.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>CO>[CH2:32]([N:39]1[CH2:30][CH:27]2[O:26][CH:25]([CH2:29][CH2:28]2)[CH2:24]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 866027052,5-Bis(hydroxymethyl)tetrahydrofuran bis(p-toluenesulfonate)

Produkt 1

HCID 120692303-Benzyl-8-oxa-3-azabicyclo[3.2.1]octaneAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2,5-bis(hydroxymethyl)tetrahydrofuran bis(p-toluenesulfonate) (10 g) and benzylamine (9.7 g) was stirred at 70° C. for 24 hours. To the mixture was added a solution of sodium hydroxide (1.85 g) in methanol (30 ml). After stirring at room temperature for 30 minutes, the mixture was filtered. The filtrate was evaporated, added dichloromethane, and filtered. The filtrate was evaporated under reduced pressure, and purified with column chromatography (silica gel, 250 ml, ethyl acetate:hexane=1:4) to give 3-benzyl-8-oxa-3-azabicyclo[3.2.1]octane (4.05 g) as an oil.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 30 minutes
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated
  4. additionadded dichloromethane
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. custompurified with column chromatography (silica gel, 250 ml, ethyl acetate:hexane=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-2a0b9c05e11c4c1f9fedb899130cd66c
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166598B2

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