Sodium hydride → tert-Butyl benzyloxy(4-cyanobutyl)carbamate

HRID 704485

Reaktionsgleichung

Reaktionsgleichung von HRID 704485
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25].CCOC(C)=O.C(Cl)(Cl)Cl>CN(C=O)C.[I-].[Na+]>[CH2:3]([O:10][N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 804745-ChlorovaleronitrileHCID 736159Tert-butyl N-(benzyloxy)carbamateHCID 21584013Chloroform ethylacetate

Produkt 1

HCID 10685938tert-Butyl benzyloxy(4-cyanobutyl)carbamateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium iodide (84 mg, 0.56 mmol) and then sodium hydride (80% oil dispersion, 0.49 g, 16.3 mmol) were added to (A) (2.68 g, 12.0 mmol) in dry DMF (40 mL). After stirring 15 min, 5-chlorovaleronitrile (1.5 mL, 13.3 mmol) was added, and the suspension heated at 80°-85° C. for 4 h under argon. After cooling, the reaction was quenched with H2O (100 mL), then extracted with ether (4×75 mL). The combined organic layers were washed with 100 mL each of 1% aqueous Na2SO3, H2O and brine and then concentrated to give 4.39 g crude product. Column chromatography with 4.5% EtOAc/CHCl3 produced 3.17 g of (B) (87% yield): NMR δ 1.5-1.75 (s+m, 13 H), 2.3 (t, 2 H), 3.4 (t, 2 H), 4.77 (s, 2 H), 7.3 (s, 5 H). Anal. Calcd for C17H24N2O3 : C, 67.08; H, 7.95; N, 9.20. Found: C, 67.19; H, 7.99; N, 9.11.

Aufarbeitung

  1. temperaturethe suspension heated at 80°-85° C. for 4 h under argon
  2. temperatureAfter cooling
  3. customthe reaction was quenched with H2O (100 mL)
  4. extractionextracted with ether (4×75 mL)
  5. washThe combined organic layers were washed with 100 mL each of 1% aqueous Na2SO3, H2O and brine
  6. concentrationconcentrated
  7. customto give 4.39 g crude product

Quellen und Nachweise

ORD-Eintrag
ord-92a422d47a9f49159fd7a756b9bf6f5e
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04987253

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