Methanol → HCID 21912718, Verbindung

HRID 1245594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245594
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:21])[C:15](=[N+]=[N-])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][OH:23]>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:21])[CH:15]([O:23][CH3:22])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 73853093HCID 73853093, Verbindung

Produkt 1

HCID 21912718HCID 21912718, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 423677Acetic acid, rhodium salt (4:2)Katalysator

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of 532 mg (1.8 mmol) of 1-(tert-butoxycarbonyl)-4-(2-diazo-1,3-dioxo-but-1-yl)piperidine in 5 mL of MeOH was treated with 25 mg (0.056 mmol) of rhodium (II) acetate dimer. The reaction was slowly warmed to 65° C. over 2 hours. Upon cooling, volatiles were removed under reduced pressure. The residue was partitioned between 100 mL of EtOAc and 100 mL of H2O. After separating phases, the organic layer was washed with 100 mL of brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 19:1 v/v hexanes/acetone as the eluant to afford the title compound as a yellow oil: RF: 0.39 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.45, 1.47 (2s, 9H), 1.68–1.71 (m, 3H), 2.19, 2.22 (2s, 3H), 2.78–2.89 (m, 2H), 3.44, 3.58 (2s, 3H), 4.03–4.3 (m, 2H).

Aufarbeitung

  1. temperatureUpon cooling
  2. customvolatiles were removed under reduced pressure
  3. customThe residue was partitioned between 100 mL of EtOAc and 100 mL of H2O
  4. customAfter separating phases
  5. washthe organic layer was washed with 100 mL of brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-68d81844e6e2457b9d09cd8ae01eeca0
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125887B2

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