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Triethylamine → (S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 1919178
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1919178
I[C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:4][CH:3]=1.C(N(CC)CC)C.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27]>CN(C=O)C.[Cu]I.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>[CH3:29][Si:28]([C:26]#[C:27][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:4][CH:3]=1)([CH3:31])[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 58498756(S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Produkt 1

HCID 58498689(S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1 g, 2.75 mmol), triethylamine (1.92 mL, 13.8 mmol) and copper(I) iodide (0.105 g, 0.551 mmol) in DMF (30 mL) was degassed under vacuum and backfilled with nitrogen. Ethynyltrimethylsilane (1.35 g, 13.8 mmol) and Pd(Ph3P)4 (0.159 g, 0.138 mmol) were added and then the reaction was sealed and heated at 50° C. for 1d. The reaction was concentrated to remove the volatiles and the residue was purified on a BIOTAGE® (silica gel, eluted with 0 to 40% ethyl acetate/hexanes) to yield (S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (751 mg, 2.25 mmol, 82% yield) as brownish foam.

Aufarbeitung

  1. customthe reaction was sealed
  2. concentrationThe reaction was concentrated
  3. customto remove the volatiles
  4. customthe residue was purified on a BIOTAGE® (silica gel, eluted with 0 to 40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-babfd1c522f9437c89b7ff1469a0b8a8
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08618153B2

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