Diisopropyl diazene-1,2-dicarboxylate → N,N'-bis(isopropoxycarbonyl)-2-acetyl-2-hydrazinocyclopentanone

HRID 1441951

Reaktionsgleichung

Reaktionsgleichung von HRID 1441951
[C:1]([CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])(=[O:3])[CH3:2].[N:10]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[N:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13]>C1(C)C=CC=CC=1>[CH:15]([O:14][C:12]([N:11]([C:4]1([C:1](=[O:3])[CH3:2])[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])[NH:10][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[O:13])([CH3:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 984712-Acetylcyclopentanone

Produkt 1

HCID 68539554N,N'-bis(isopropoxycarbonyl)-2-acetyl-2-hydrazinocyclopentanoneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-acetyl-cyclopentanone (13.9 mg, 0.11 mol) and (R,R)-trans-1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(N,N-dimethylamino)cyclohexyl]thiourea (4.1 mg, 0.01 mmol) in toluene (1 mL) was added diisopropyl azodicarboxylate (21.5 μL, 0.10 mmol) at −78° C. After stirring for 18 hr, the reaction mixture was concentrated. The residue was purified by silica gel column (hexane/ethyl acetate=3/1) to give the title compound (31.8 mg, yield: 97%, optical purity: 77% ee). Colorless oil

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by silica gel column (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-0234bbdea17e4589af7805259bc7c25c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655817B2

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