Triethylamine → HCID 86602061, Verbindung

HRID 1295378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295378
C(N(CC)CC)C.[F:8][C:9]([F:25])([F:24])[C:10]1[CH:11]=[C:12]([CH:20]([NH:22][CH3:23])[CH3:21])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[C:38]([O:42][C:43](=[O:57])[NH:44][C@@:45]12[CH2:50][CH:49]1[CH2:48][NH:47][C@H:46]2[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([CH3:41])([CH3:40])[CH3:39].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(#N)C>[C:38]([O:42][C:43](=[O:57])[NH:44][C@@:45]12[CH2:50][CH:49]1[CH2:48][N:47]([C:30](=[O:36])[N:22]([C@H:20]([C:12]1[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=[C:10]([C:9]([F:8])([F:24])[F:25])[CH:11]=1)[CH3:21])[CH3:23])[C@H:46]2[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)([CH3:41])([CH3:39])[CH3:40]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 220173563,5-Bis(trifluoromethyl)-alpha,N-dimethylbenzylamineHCID 69336084HCID 69336084, Verbindung

Produkt 1

HCID 86602061HCID 86602061, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a round bottom flask was added methylene chloride (8 mL), triethylamine (0.87 mL, 6.3 mmol), and [(SR)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methyl-amine (0.49 g, 1.6 mmol. The mixture was cooled to 0° C. and triphosgene (0.18 g, 0.61 mmol) in methylene chloride (3 mL) was added dropwise. The clear solution was stirred for 16 hours at room temperature. To the reaction mixture was added racemic Intermediate 48, one enantiomer being ((1S,2S)-2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-carbamic acid tert-butyl ester (0.40 g, 1.5 mmol), diisopropyl ethyl amine (0.25 mL, 1.5 mmol), and acetonitrile (8 mL). The reaction was heated to remove the methylene chloride and then refluxed for 2 hours. The solvent was removed at reduced pressure and the residue was partitioned between saturated citric acid solution and methylene chloride. The organic phase was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered, and concentrated to give the title compounds as a foam (0.84 g, quantitative yield).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. customto remove the methylene chloride
  3. temperaturerefluxed for 2 hours
  4. customThe solvent was removed at reduced pressure
  5. customthe residue was partitioned between saturated citric acid solution and methylene chloride
  6. washThe organic phase was washed with saturated sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ee0fdaa97fef495bbf2e93c8464d91bf
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241798B2

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