Reaktion #1272

Reaktionsgleichung

dimethylamine

Nε-dimethylamino-Nα-CBZ-O-t-butyl L-lysine

hydrogen peroxide

hydrogen peroxide

→

product

Nε-dimethylamino-Nα-CBZ-O-t-butyl L-lysine N-oxide

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Wascheneluting with solvent A
3. 3
   workup.ADDITIONA 1 mL aqueous slurry of approximately 5 mg of platinum black was added whereupon the reaction
4. 4
   workup.STIRRINGwas stirred for 7 h
5. 5
   workup.ADDITIONanother slurry of 5-10 mg platinum black added
6. 6
   workup.STIRRINGThe mixture was stirred overnight
7. 7
   Sonstigeto remove peroxides when necessary
8. 8
   Filtrationthe mixture was filtered
9. 9
   Einengenconcentrated
10. 10
    workup.DISSOLUTIONThe residue was dissolved into 300 mL of EtOAc
11. 11
    Trocknendried over Na2SO4
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated
14. 14
    Sonstigechromatographed on 400 g of silica gel
15. 15
    Wascheneluting with Solvent A

Vorschrift

A solution of 25.3 g of dimethylamine 2, 7.9 mL of 30% hydrogen peroxide and 150 mL of methanol was stirred for 5 h after which an additional 7.9 g of 30% hydrogen peroxide was added. The reaction was allowed to stir for 48 h and monitored by silica gel TLC, eluting with solvent A. A 1 mL aqueous slurry of approximately 5 mg of platinum black was added whereupon the reaction was stirred for 7 h and another slurry of 5-10 mg platinum black added. The mixture was stirred overnight and monitored for peroxides using peroxide test paper with warming to 60° C. to remove peroxides when necessary. Once the reaction tested negative for peroxides, the mixture was filtered and concentrated. The residue was dissolved into 300 mL of EtOAc, dried over Na2SO4, filtered, concentrated and chromatographed on 400 g of silica gel, eluting with Solvent A to produce 13 g of product as a colorless oil.

Quelle