Quinoline → (Z)-tert-butyl 4-(3-Hydroxyprop-1-enyl)piperidine-1-carboxylate

HRID 1468816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468816
[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.N1C2C(=CC=CC=2)C=CC=1>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][CH2:2]/[CH:3]=[CH:4]\[CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Komponenten

5

Edukt 2

HCID 7047QuinolineHCID 69786345Tert-butyl 4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 90115537(Z)-tert-butyl 4-(3-Hydroxyprop-1-enyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The alkyne from step B (6.5 g, 27.2 mmol) and quinoline (0.55 mL, 4.62 mmol) were dissolved in EtOAc (120 mL). Lindlar's catalyst (740 mg) was added and the reaction was stirred under hydrogen atmosphere (1 atm) for 40 minutes. The reaction was filtered and concentrated to yield a crude residue which was purified by silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes) to yield the desired allylic alcohol. 1H NMR (500 MHz, CDCl3) δ 5.58 (m, 1H), 5.37 (dd, J 10.8 & 9.6 Hz, 1H), 4.22 (d, 2H), 4.16-3.99 (m, 2H), 2.80-2.78 (m, 2H), 2.52-2.40 (m, 1H), 1.61-1.56 (m, 2H), 1.45 (s, 9H), 1.36-1.22 (m, 2H).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto yield a crude residue which
  4. customwas purified by silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-097bc55351ac4f86b1d82a74a9c4a25a
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006228B2

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