1-Bromo-2-methylpropane → tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate

HRID 976625

Reaktionsgleichung

Reaktionsgleichung von HRID 976625
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:19](Br)[CH:20]([CH3:22])[CH3:21]>CN(C)C=O>[CH2:3]([O:10][N:11]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamate

Produkt 1

HCID 19967428tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamateAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium hydride (0.97 g of 80% in mineral oil, 32 mmol) was added to a solution of tert-butyl N-benzyloxycarbamate (6.53 g, 29 mmol) in N,N-dimethylformamide (45 mL). A gas evolved and the mixture was stirred for 20 minutes. Isobutyl bromide (3.5 mL, 32 mmol) was added and the reaction mixture was heated at 70° C. for 1.5 hr. The reaction was quenched with water (about 50 mL) then extracted twice with diethyl ether. The extracts were combined, washed with water (5 small portions), dried over magnesium sulfate and then concentrated under vacuum to provide 7.63 g of tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate as a faintly brown oil.

Aufarbeitung

  1. customThe reaction was quenched with water (about 50 mL)
  2. extractionthen extracted twice with diethyl ether
  3. washwashed with water (5 small portions)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3dd3f6a213ec4bc4b90a3cd5f9f2619b
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612377

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