Methyl iodide → tert-butyl N-benzyloxy-N-methylcarbamate

HRID 976631

Reaktionsgleichung

Reaktionsgleichung von HRID 976631
[H-].[Na+].C(ONC(=O)OC(C)(C)C)C1C=CC=CC=1.[C:19]([O:23][C:24](=[O:38])[N:25]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:26]C(C)C)([CH3:22])([CH3:21])[CH3:20].IC>CN(C)C=O>[CH2:31]([O:30][N:25]([CH3:26])[C:24](=[O:38])[O:23][C:19]([CH3:20])([CH3:21])[CH3:22])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamateHCID 19967428tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate

Produkt 1

HCID 14227181tert-butyl N-benzyloxy-N-methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (0.48 g of 80% in mineral oil, 16 mmol) was added to a solution of tert-butyl N-benzyloxycarbamate (Compound 54 Part A, 3 g, 13 mmol) in N,N-dimethylformamide (25 mL). The reaction mixture was stirred for 20 minutes then iodomethane (1.1 mL, 18 mmol) was added dropwise with cooling in an ice bath. The resulting suspension was stirred at ambient temperature under a nitrogen atmosphere overnight. The reaction mixture was quenched with water (50 mL) then extracted with diethyl ether (150 mL). The organic layer was washed with water (5×50 mL), dried over magnesium sulfate then concentrated to provide 3.1 g of tert-butyl N-benzyloxy-N-methylcarbamate as a yellow oil.

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. stirringThe resulting suspension was stirred at ambient temperature under a nitrogen atmosphere overnight
  3. customThe reaction mixture was quenched with water (50 mL)
  4. extractionthen extracted with diethyl ether (150 mL)
  5. washThe organic layer was washed with water (5×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3b5ac8a5b1854f79944972dfbdf8fb6b
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612377

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