Heptane → HCID 178516032, Verbindung

HRID 228339

Reaktionsgleichung

Reaktionsgleichung von HRID 228339
B(Br)(Br)Br.CCCCCCC.C[O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C@H:23]2[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]2)=[CH:16][CH:15]=1>C(Cl)Cl>[OH:29][C@H:26]1[CH2:27][CH2:28][C@H:23]([NH:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([OH:13])=[CH:19][CH:18]=2)[CH2:24][CH2:25]1

Komponenten

5

Edukt 3

HCID 8900HeptaneHCID 25134Boron tribromideHCID 178490342HCID 178490342, Verbindung

Produkt 1

HCID 178516032HCID 178516032, VerbindungAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add dropwise 1.0 M BBr3 in heptane (1.35 mL, 1.35 mmol) to a suspension of (±)-(trans)-4-[2-(4-methoxyphenyl)ethylamino]cyclohexanol (Part A, 153.2 mg, 0.61 mmol) in anhydrous CH2C12 (5.0 mL) at 0° C. Add another 1.0 mL of CH2Cl2 when the compound precipitates out. Stir the mixture at 0° C. for 30 minutes and at room temperature for 2 hours. Quench the reaction with 5 drops of H2O and concentrate. Purify the residue on an SCX column, washing with MeOH and then eluting with 2.0 M NH3 in MeOH to yield (±)-(trans)-4-[2-(4-hydroxycyclohexylamino)ethyl]phenol (121.2 mg).

Aufarbeitung

  1. customprecipitates out
  2. waitat room temperature for 2 hours
  3. customQuench
  4. customthe reaction with 5 drops of H2O
  5. concentrationconcentrate
  6. customPurify the residue on an SCX column
  7. washwashing with MeOH
  8. washeluting with 2.0 M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-c97f2811532449d8a62f5284b1f9ee26
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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