HCID 86717460, Verbindung → HCID 86717461, Verbindung

HRID 712001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712001
[C:1]([O:4][CH2:5][CH:6]([O:9][CH2:10][C@@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH2:13])C=C)(=[O:3])[CH3:2]>C(=[Ru](Cl)(Cl)([C-]1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH:6]1[CH:13]=[CH:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:10][O:9]1)(=[O:3])[CH3:2]

Komponenten

3

Edukt 1

HCID 86717460HCID 86717460, Verbindung

Produkt 1

HCID 86717461HCID 86717461, VerbindungAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178425457HCID 178425457, VerbindungKatalysator

Versuchsvorschrift

To a 500 mL 2-neck round bottom flask, benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)ruthenium (38 mg, 0.044 mmol) was added. After purged with nitrogen for 3 times, dichloromethane (anhydrous, 8 mL) was added followed by 2-({(2S)-2-[(tert-butoxycarbonyl)amino]but-3-en-1-yl}oxy)but-3-en-1-yl acetate (265 mg, 0.885 mmol). The reaction mixture was stirred at room temperature for 15 h. The mixture was concentrated in vacuo. The residue was purified via flash chromatography (eluting with hexanes to 25% EtOAc in hexanes) to give the desired product as a brown oil (0.205 g, 85%). LCMS calculated for C9H14NO5 (M+H-Bu+H)+: m/z=216.1. Found: 216.1. 1H NMR (300 MHz, CDCl3) δ 5.94 (0.17H, m), 5.84 (0.83H, m), 5.69 (1H, m), 4.89 (0.13H, m), 4.70 (0.83H, m), 4.25 (1H, m), 4.05 (4H, m), 3.56 (0.13H, m), 3.38 (0.87H, m), 2.04 (2.49H, s), 2.03 (0.51H, m), 1.38 (9H, s) ppm (The product was a ˜5:1 mixture of trans- and cis-isomers).

Aufarbeitung

  1. customAfter purged with nitrogen for 3 times, dichloromethane (anhydrous, 8 mL)
  2. additionwas added
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified via flash chromatography (eluting with hexanes to 25% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-acec4cde13654fb68ae2fa049c74920e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181271B2

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