Methyl iodide → Benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 371280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 371280
[Cl:1][C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH:20]([N-]C(C)C)(C)C.[Li+].CI.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:20][CH:6]1[C:5](=[O:9])[N:4]2[CH:7]1[CH2:8][C:2]([Cl:1])=[C:3]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 12804728Benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2carboxylate

Produkt 1

HCID 15136304Benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (56 mg) in anhydrous THF (0.5 ml) is added dropwise over a few minutes to a stirring solution of lithium diisopropylamide (from 31 μl diisopropylamine and 140 μl 1.6N BuLi) in anhydrous THF (3 ml) at -78°. After 15 more mins at -78°, the solution is treated with methyliodide (125 μl) and then allowed to warm to -20° over a period of 30 mins. Saturated aqueous NH4Cl (3 ml) is added and the mixture is allowed to come to room temperature. The mixture is diluted with EtOAc (50 ml), washed with pH 3 phosphate buffer, water, 5% NaHCO3, and brine, dried with magnesium sulfate, and evaporated in vacuo to give benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Aufarbeitung

  1. temperatureto warm to -20° over a period of 30 mins
  2. customto come to room temperature
  3. washwashed with pH 3 phosphate buffer, water, 5% NaHCO3, and brine
  4. dry with materialdried with magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fa0a129754d64ccd8b58d4106b86fe1f
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04530841

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