Toluene → 4-(5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

HRID 872198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872198
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:24])[CH2:15][C:16]2[C:21](Br)=[CH:20][N:19]=[C:18]([Cl:23])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:24][C:21]3=[CH:20][N:19]=[C:18]([Cl:23])[CH:17]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 866748964-[2-(5-Bromo-2-chloropyridin-4-yl)-1-hydroxy-ethyl]piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866748954-(5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 4-[2-(5-bromo-2-chloro-pyridin-4-yl)-1-hydroxy-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (11.60 g), palladium acetate (0.50 g), racemic 2-(di-tert-butylphosphino)-1,1′-binapthyl (1.00 g), cesium carbonate (14.00 g), and toluene (150 mL) is stirred at 110° C. under argon atmosphere for 5 h. After cooling to room temperature, ethyl acetate and water are added. The organic phase is separated, washed with brine, dried (MgSO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→50:50) to give the title compound. Mass spectrum (ESI+): m/z=339/341 (Cl) [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase is separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→50:50)

Quellen und Nachweise

ORD-Eintrag
ord-d09793cd79aa45488a33238cfa599212
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975277B2

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