Triethylamine → Ethyl 3-[4-(N-BOC-4-hydroxypiperidin-4-yl)phenyl]crotonate

HRID 265872

Reaktionsgleichung

Reaktionsgleichung von HRID 265872
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:22]([O:27][CH2:28][CH3:29])(=[O:26])/[CH:23]=[CH:24]/[CH3:25].CCN(CC)CC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].CC#N>[C:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18](/[C:24](/[CH3:25])=[CH:23]\[C:22]([O:27][CH2:28][CH3:29])=[O:26])=[CH:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 429065Ethyl trans-crotonateHCID 183795571-Boc-4-(4-bromo-phenyl)-piperidin-4-ol

Produkt 1

HCID 67721045Ethyl 3-[4-(N-BOC-4-hydroxypiperidin-4-yl)phenyl]crotonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 10-3 (500 mg, 1.4 mmoles), ethyl crotonate (1.7 mL, 3.8 mmoles), Pd(OAc)2 (31 mg, 0.14 mmoles), NEt3 (0.78 mL, 8 mmoles), tri-o-tolylphosphine (170 mg, 0.56 mmoles), and CH3CN (7 mL) was heated in a sealed tube at 100° C. for 24 hours. The cooled reaction mixture was diluted with EtOAc and then washed with H2O, 10% KHSO4, saturated NaHCO3, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 25% EtOAc/hexanes) gave 12-1 as a waxy yellow solid. Rf 0.33 (silica, 25% EtOAc/hexanes).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. washwashed with H2O, 10% KHSO4, saturated NaHCO3, and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-70bb63e1460c4ec5924b2eb1a4f52944
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648368

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