Trifluoroacetic acid → O-Benzyl-N-(4-cyanobutyl)hydroxylamine

HRID 704486

Reaktionsgleichung

Reaktionsgleichung von HRID 704486
FC(F)(F)C(O)=O.[CH2:8]([O:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-]S([O-])(=O)=O.[Ca+2]>CCO.C(Cl)(Cl)Cl>[CH2:8]([O:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 24497Calcium SulfateHCID 10685938tert-Butyl benzyloxy(4-cyanobutyl)carbamate

Produkt 1

HCID 14078488O-Benzyl-N-(4-cyanobutyl)hydroxylamineAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21889567Chloroform ethanolLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (TFA, 16 mL) was added to (B) (2.59 g, 8.51 mmol), and the solution stirred at room temperature for 20 min (Drierite tube). Excess TFA was removed on the rotovap, saturated NaHCO3 (50 mL) was added and the product was extracted into ether (3×50 mL). After a brine wash (50 mL), the organic extracts were concentrated to yield 1.77 g crude product. Column chromatography with 3% EtOH/CHCl3 furnished 1.31 g of (3) (75% yield), which has been previously prepared: NMR δ1.5-1.7 (m, 4 H), 2.16-2.35 (m, 2 H), 2.78-2.98 (m, 2 H), 4.66 (s, 2 H), 5.45 (br s, 1 H), 7.28 (s, 5 H).

Aufarbeitung

  1. customExcess TFA was removed on the rotovap, saturated NaHCO3 (50 mL)
  2. additionwas added
  3. extractionthe product was extracted into ether (3×50 mL)
  4. washAfter a brine wash (50 mL)
  5. concentrationthe organic extracts were concentrated
  6. customto yield 1.77 g crude product

Quellen und Nachweise

ORD-Eintrag
ord-5f0eedc7ac5547d2b7e1c4d04400cc41
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04987253

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