N,N,N',N'-Tetramethylethylenediamine → HCID 69264112, Verbindung

HRID 1593014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593014
CN(C)CCN(C)C.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][C:41](/[CH:44]=[CH:45]/[C:46]([N:48]2[C@H:52]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@H:51]([CH3:59])[N:50]([CH3:60])[C:49]2=[O:61])=[O:47])=[CH:40][CH:39]=1)(=[O:37])=[O:36]>C1COCC1.[Cu]I>[CH3:34][S:35]([C:38]1[CH:39]=[CH:40][C:41]([C@H:44]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:45][C:46]([N:48]2[C@H:52]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@H:51]([CH3:59])[N:50]([CH3:60])[C:49]2=[O:61])=[O:47])=[CH:42][CH:43]=1)(=[O:36])=[O:37]

Komponenten

7

Edukt 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 69238885HCID 69238885, VerbindungHCID 178418255HCID 178418255, VerbindungHCID 178418657HCID 178418657, Verbindung

Produkt 1

HCID 69264112HCID 69264112, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of copper (I) iodide (960 mg, 5.0 mmol) and THF (20 mL) was added N,N,N′,N′-tetramethylethylenediamine (0.83 mL, 5.5 mmol) and the resulting mixture was stirred at room temperature for 10 min. then cooled to −78° C. Phenylmagnesium bromide (5.0 mL, 1M in THF, 5.0 mmol) was added and the resulting mixture stirred at −78° C. for 15 min. A solution of di-n-butylboron triflate (3.0 mL, 1M in diethyl ether, 3.0 mmol) and (E)-(4S,5R)-1-(3-[4-methanesulfonylphenyl]acryloyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (Method D, 1.0 g, 2.51 mmol) in THF (15 mL) was added and the resulting mixture was stirred whilst allowing to warm to room temperature for 18 h. The reaction mixture was washed with saturated aqueous ammonium chloride, water and brine, dried (MgSO4) and evaporated. The residue was purified by eluting through a 20 g Bond Elut with gradient of isohexane to ethyl acetate giving the sub-titled compound (1.49 g, 100%); NMR (CDCl3): 0.78 (d, 3H), 2.82 (s, 3H), 3.00 (s, 3H), 3.78 (dd, 1H), 3.80 (m, 1H), 3.98 (dd, 1H), 4.72 (m, 1H), 5.19 (d, 1H), 6.99 (m, 2H), 7.22 (m, 8H), 7.48 (d, 2H), 7.79 (d, 2H); MS: 477 (MH+).

Aufarbeitung

  1. temperaturethen cooled to −78° C
  2. stirringthe resulting mixture stirred at −78° C. for 15 min
  3. stirringthe resulting mixture was stirred
  4. temperatureto warm to room temperature for 18 h
  5. washThe reaction mixture was washed with saturated aqueous ammonium chloride, water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified
  9. washby eluting through a 20 g Bond Elut with gradient of isohexane to ethyl acetate giving the sub-titled compound (1.49 g, 100%)

Quellen und Nachweise

ORD-Eintrag
ord-d9aa373b8dd843ceb872890c7551b714
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294636B2

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