Dimethylformamide → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 538735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538735
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C#C.CC[N:19](CC)[CH2:20][CH3:21].C[N:25](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>[NH:25]1[CH:21]=[CH:20][N:19]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6326AcetyleneHCID 8471TriethylamineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Produkt 1

HCID 49783269tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4 (0.78 g, 1.7 mmol), acetylene intermediate A5 (0.56 g, 1.7 mmol, synthesized as described in Scheme 1-1), CuI (63 mg, 0.33 mmol), and Et3N (0.67 mL, 5.0 mmol) in DMF (20 mL) was added Pd(PPh3)4 (0.19 g, 0.165 mmol). The resulting mixture was degassed with N2, and then stirred at 100° C. overnight in a sealed tube. The reaction mixture was slowly dropped into H2O (100 mL). The precipitate was collected and then dissolved in EtOAc. The organic phase was dried, filtered, and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (EtOAc) to afford 5 (420 mg, 34% yield). LC-MS (ESI): m/z 746.4 (M+H)+

Aufarbeitung

  1. customThe resulting mixture was degassed with N2
  2. additionThe reaction mixture was slowly dropped into H2O (100 mL)
  3. customThe precipitate was collected
  4. dissolutiondissolved in EtOAc
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue, which
  9. customwas purified by silica gel column chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a3a82204f86140158d54f4c1312aaad7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865756B2

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