Tetrahydrofuran → HCID 70153172, Verbindung

HRID 277777

Reaktionsgleichung

Reaktionsgleichung von HRID 277777
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH:13]=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[CH3:17][C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH3:31])[CH2:20][NH:19]1.O1CCCC1.C([BH3-])#N.[Na+]>CO.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:19]3[CH2:20][C@@H:21]([CH3:31])[N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:23][C@@H:18]3[CH3:17])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 24903576(2R,5S)-2,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 70153172HCID 70153172, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11026Titanium isopropoxideKatalysatorHCID 702EthanolLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a round bottom flask were added 1-(4-cyanobenzyl)-5-formylimidazole (250.0 mg, 1.2 mmole) along with titanium(IV)isopropoxide (1.0 ml, 3.65 mmol), (trans) 2,5-Dimethyl-4-tertbutyloxycarbonylpiprizine (253.7 mg, 1.2 mmol) (prepared as described in Step 1), and tetrahydrofuran (0.4 ml). The reaction was heated at 60° C. for 1.25 hour. The reaction was cooled and sodiumcyanoborohydride (95.0 mg, 1.5 mmol) was added along with ethanol (0.5 ml) and the reaction was stirred at RT for 18 hours. The reaction was diluted with methanol/water (3 ml/1 ml) and the mixture filtered through celite. The filtrate was then concentrated to an oil, dissolved into methanol and put through a High Pressure Liquid Chromatography column. The desired fractions were collected, concentrated, and lyophilized to give the ditrifluoroacetic acid salt of the title compound.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationthe mixture filtered through celite
  3. concentrationThe filtrate was then concentrated to an oil
  4. dissolutiondissolved into methanol
  5. customThe desired fractions were collected
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-746d9af315ab4fb7a69c9a5a5da08560
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358956B1

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