Methyl iodide → HCID 54406880, Verbindung

HRID 617758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617758
[C:1]([NH:11][C@@H:12]([CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23]I.[H-].[Na+]>CN(C=O)C>[C:1]([N:11]([C@@H:12]([CH3:22])[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[CH3:23])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54393776HCID 54393776, Verbindung

Produkt 1

HCID 54406880HCID 54406880, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

A solution of (S)-(-)-N-carbobenzyloxy-α-methyl-4-nitrobenzylamine (8.2 gm, 28 mmol) and methyl iodide (2.6 mL, 42 mmol) in DMF (50 mL) was cooled under nitrogen in an ice bath to 5-10° C. and sodium hydride (60% suspension in mineral oil) (1.2 gm, 31 mmol) was added in portions over 15 min while maintaining the temperature at 5-10° C. The reaction was stirred for 1 hr and then slowly quenched into a mixture of ice water, 2N hydrochloric acid (20 mL) and ether and the layers were separated. The ether layer was washed with water and brine and the aqueous layers were consecutively extracted with a second portion of ether. The pooled ether layers were dried over sodium sulfate and evaporated. The residue was purified by flash chromatography using 10-30% ethyl acetate/hexanes to give 6.6 gm (77%) of the title compound. [α]D (EtOH)=-97°.

Aufarbeitung

  1. customslowly quenched into a mixture of ice water, 2N hydrochloric acid (20 mL) and ether
  2. customthe layers were separated
  3. washThe ether layer was washed with water and brine
  4. extractionthe aqueous layers were consecutively extracted with a second portion of ether
  5. dry with materialThe pooled ether layers were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c48c07716b9e4b96a5201d5d6a650188
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952321

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