Triethylamine → HCID 69950662, Verbindung

HRID 381742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381742
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:10][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)O)[CH2:6]1.COCO[C@H]1CCN([C@H](C2C=CC=CC=2)CO)C1.C(N(CC)CC)C.CS(Cl)(=O)=O.[H-].[Na+].[Cl:51][C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][C:59]=1[NH:60][CH3:61])[C:55]#[N:56].[NH4+].[OH-]>C(Cl)Cl.CN(C)C=O.O>[Cl:51][C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][C:59]=1[N:60]([C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][N:7]1[CH2:8][CH2:9][C@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6]1)[CH3:61])[C:55]#[N:56]

Komponenten

11

Edukt 7

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 15520998HCID 15520998, VerbindungHCID 15520999HCID 15520999, VerbindungHCID 159077543-Chloro-4-(methylamino)benzonitrile

Produkt 1

HCID 69950662HCID 69950662, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of the mixture of 2-(3-(S)-methoxymethoxypyrrolidin-1-yl)-1-(S)-phenylethanol and 2-(3-(S)-methoxymethoxypyrrolidin-1-yl)-2-(R)-phenylethanol (251 mg, 1.00 mmol) and triethylamine (0.167 ml, 1.20 mmol) in CH2Cl2 (4 ml) was added methanesulfonyl chloride (0.093 ml, 1.20 mmol) dropwise at 0° C. (ice bath). After 15.5 h stirring at room temperature, the reaction mixture was washed with saturated NaHCO3 aqueous solution, brine, dried (Na2SO4), and concentrated to give 238 mg of brown viscous oil-(i). To a suspension of NaH (48 mg, 1.20 mmol) in N,N-dimethylformamide (2 ml) was added a solution of 3-chloro-4-methylaminobenzonitrile (200 mg, 1.20 mmol) at room temperature. After stirring for 45 min, to this mixture was added a solution of the above brown viscous oil-(i) in N,N-dimethylformamide (2 ml) at room temperature and the mixture was stirred at room temperature for 4.5 h. H2O was added to this mixture, basified with 25%-NH4OH and extracted with CH2Cl2. The extract was washed with water, brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel; 20 g, CH2Cl2/MeOH: 100/1-50/1) to afford 244 mg (61%) of brown oil.

Aufarbeitung

  1. washthe reaction mixture was washed with saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give 238 mg of brown viscous oil-(i)
  5. stirringAfter stirring for 45 min, to this mixture
  6. stirringthe mixture was stirred at room temperature for 4.5 h
  7. extractionextracted with CH2Cl2
  8. washThe extract was washed with water, brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto give brown oil, which
  12. customwas purified by column chromatography (silica gel; 20 g, CH2Cl2/MeOH: 100/1-50/1)

Quellen und Nachweise

ORD-Eintrag
ord-fa1c4275bf0247a4b3a53a48b1abb002
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307061B2

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