Triethylamine → HCID 178454058, Verbindung

HRID 2370738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370738
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32][C:33]1[C:42]([OH:43])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH:35]=[CH:36][N:37]=[CH:38]2.[C:44]([O:48][C:49](=[O:58])[NH:50][C@H:51]1[CH2:56][CH2:55][C@H:54](O)[CH2:53][CH2:52]1)([CH3:47])([CH3:46])[CH3:45].C(N(CC)CC)C>ClCCl>[C:44]([O:48][C:49](=[O:58])[NH:50][C@H:51]1[CH2:52][CH2:53][C@@H:54]([O:43][C:42]2[C:33]([Br:32])=[C:34]3[C:39](=[CH:40][CH:41]=2)[CH:38]=[N:37][CH:36]=[CH:35]3)[CH2:55][CH2:56]1)([CH3:47])([CH3:45])[CH3:46]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1360928955-Bromo-6-isoquinolinolHCID 178418329HCID 178418329, Verbindung

Produkt 1

HCID 178454058HCID 178454058, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4.33 mL (5.75 g, 33 mmol) of diethyl azo dicarboxylate were added to 18 g (68.75 mmol) of triphenylphosphine in 500 mL of dichloromethane at 0° C. and stirred for 15 min. 6.16 g (27.5 mmol) 5-bromo-isoquinolin-6-ol (2), 5.92 g (27.5 mmol) (trans-4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester and 3.81 mL (33 mmol) triethyl amine were added. The mixture was stirred for 4 days. The precipitate was removed by filtration, washed with dichloromethane and the solvents were distilled off. The crude product was purified by flash chromatography using ethyl acetate/n-heptane as eluent to give 2.77 g (24%) of 85. Rt=1.37 min (Method #1). Detected mass: 421.1/423.1 (M+H+).

Aufarbeitung

  1. stirringThe mixture was stirred for 4 days
  2. customThe precipitate was removed by filtration
  3. washwashed with dichloromethane
  4. distillationthe solvents were distilled off
  5. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3aab3c1c684343d38bf9afa73cc048c1
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710228B2

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