Water → Boc4-aminomethylbicyclo-[2.2.2]octane nitrile

HRID 365276

Reaktionsgleichung

Reaktionsgleichung von HRID 365276
[C:1]([CH:8]1[CH2:13][C:12]2([CH2:16][NH2:17])[CH2:14][CH2:15][C:9]1([C:18]([NH2:20])=O)[CH2:10][CH2:11]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.C(Cl)(Cl)Cl.CO.O.O>C(Cl)Cl.N1C=CC=CC=1>[C:1]([CH:8]1[CH2:13][C:12]2([CH2:16][NH2:17])[CH2:11][CH2:10][C:9]1([C:18]#[N:20])[CH2:15][CH2:14]2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 21866399Chloroform methanol waterHCID 69901712Boc-4-aminomethylbicyclo-[2.2.2]octane carboxamide

Produkt 1

HCID 69900746Boc4-aminomethylbicyclo-[2.2.2]octane nitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 7.52 g (26.6 mmol) of the product from step C in 50 ml of CH2Cl2 and 80 ml of anhydrous pyridine was treated with 11.12 g of (methoxycarbonylsulfamoyl)-triethylammonium hydroxide inner salt (Burgess reagent) in 1-g portions over 5 min. After stirring for 1.5 hr, TLC (90-10-1, CHCl3 -CH3OH-H2O) showed complete conversion to product, and the solution was evaporated to give a paste, to which H2O was added, up to 400 ml, with trituration and stirring to afford, after standing 20 hr at 0° C., filtration and drying in vacuo, the title compound as a white solid.

Aufarbeitung

  1. customthe solution was evaporated
  2. customto give a paste
  3. stirringstirring
  4. customto afford
  5. waitafter standing 20 hr at 0° C.
  6. filtrationfiltration
  7. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-569ed572bb68436eaab4e845b5eb49b9
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127333

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