Triacetoxyperiodinane → (1-Formylcyclopropyl)carbamic acid tert-butyl ester

HRID 409168

Reaktionsgleichung

Reaktionsgleichung von HRID 409168
[OH:1][CH2:2][C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[CH2:5][CH2:4]1)=[O:1]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

Produkt 1

HCID 10352385(1-Formylcyclopropyl)carbamic acid tert-butyl esterAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (Bioorg. Med. Chem. Lett., 2008, 18(6), 2188) (135 mg, 0.72 mmoles) in DCM (8 mL) was added Dess-Martin periodinane (277 mg, 0.65 mmole). After stirring 1 hr, the reaction was filtered through celite and concentrated to a yellow oil which was further purified by Isolera (7%-70% ethyl acetate/hexanes) to provide 84 mg (87%) of tert-butyl (1-formylcyclopropyl)-carbamate as a white solid.

Aufarbeitung

  1. filtrationthe reaction was filtered through celite
  2. concentrationconcentrated to a yellow oil which
  3. customwas further purified by Isolera (7%-70% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6a8cbcfd92364f9db8d0711fef89a97d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759358B1

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