N,O-Dimethylhydroxylamine → Tert-butyl 3-(methoxy(methyl)amino)-3-oxopropyl(methyl)carbamate

HRID 426032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426032
[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:27][O:28][NH:29][CH3:30]>C1COCC1>[CH3:27][O:28][N:29]([CH3:30])[C:11](=[O:13])[CH2:10][CH2:9][N:8]([CH3:14])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27609523-(Methylamino)propanoic acid, N-BOC protected

Produkt 1

HCID 59364357Tert-butyl 3-(methoxy(methyl)amino)-3-oxopropyl(methyl)carbamateAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-(tert-butoxycarbonyl(methyl)amino)propanoic acid (130 g, 0.64 mol) in anhydrous THF was added CDI at 0° C. The resulting mixture was stirred for 1 h at 0° C. To this mixture was added a solution of O,N-dimethylhydroxylamine hydrochloric salt (145.2 g, 0.9 mol) and TEA (90.1 g, 0.9 mol) in THF at rt. The resulting mixture was stirred overnight. Solvent and volatiles were removed under reduced pressure. The residue was purified via column chromatography to give tert-butyl 3-(methoxy(methyl)amino)-3-oxopropyl(methyl)carbamate (120 g, 75.5%) as a colorless oil. 1HNMR (CDCl3, 400 MHz) 1.45 (s, 9H), 2.62-2.71 (m, 2H), 2.87 (s, 3H), 3.17 (s, 3H), 3.48-3.56 (m, 2H), 3.68 (s, 3H)

Aufarbeitung

  1. stirringThe resulting mixture was stirred overnight
  2. customSolvent and volatiles were removed under reduced pressure
  3. customThe residue was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf61fd96735843c1807a425275138680
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106221B2

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