Reaktion #480592

ord-41a99d97be5e482e8c5bb07a1cfdf604

Reaktionsgleichung

CCOC(=O)/N=N/C(=O)OCC
DEAD
Cc1ccc(S(=O)(=O)NC(=O)OC(C)(C)C)cc1
N-Boc-p-toluenesulfonamide
→
Cc1ccc(S(=O)(=O)N(C)C(=O)OC(C)(C)C)cc1
N-methyl-N-boc-p-toluenesulfonamide
Ausbeute 85.0%

Edukte

CCOC(=O)/N=N/C(=O)OCC
DEAD
Cc1ccc(S(=O)(=O)NC(=O)OC(C)(C)C)cc1
N-Boc-p-toluenesulfonamide

Reagenzien

Keine

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONOnce again, the standard mode of addition

Vorschrift

The crude fluorous DEAD reagent 22 was then used in Mitsunobu reactions with N-Boc-p-toluenesulfonamide. Once again, the standard mode of addition gave complete conversion with MeOH and the product, N-methyl-N-boc-p-toluenesulfonamide was isolated in 85% yield after FSPE. However, the allyl alcohol gave only trace conversion of the starting material. The organic fraction after FSPE was mostly starting material. These results are summarized in Table 7.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06806357B1uspto-grants-2004_10