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Sodium Carbonate → Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

HRID 1622306
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1622306
Br[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:13]=3)[CH2:8]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:31]2[CH2:32][CH2:33][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:35][CH:36]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:40]([O:39][C:37]([N:34]1[CH2:33][CH:32]=[C:31]([C:2]2[CH:22]=[CH:21][C:5]([CH2:6][N:7]3[CH2:16][CH2:15][C:14]4[C:9](=[CH:10][CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:13]=4)[CH2:8]3)=[CH:4][CH:3]=2)[CH2:36][CH2:35]1)=[O:38])([CH3:43])([CH3:41])[CH3:42]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 67980521HCID 67980521, Verbindung

Produkt 1

HCID 67980088Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (200.0 mg, 0.600 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (188.8 mg, 0.6107 mmol) in DME (5.15 mL) was treated with Na2CO3 (2.00 M in water, 0.83 mL, 1.66 mmol). The mixture was degassed and Pd(Ph3P)4 (13 mg, 0.011 mmol) was added. The reaction mixture was heated under argon at 80° C. overnight. The mixture was then cooled to room temperature and diluted with water. The aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, 10-50% EtOAc in hexanes) to give methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (228 mg, 89%). LC-MS: (FA) ES+ 263.

Aufarbeitung

  1. customThe mixture was degassed
  2. temperatureThe mixture was then cooled to room temperature
  3. extractionThe aqueous phase was extracted twice with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2, 10-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f5029909870845f9ab7a80b7ea9c6466
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778931B2

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