2-Chloro-1,3,5-trimethylbenzene → HCID 59531008, Verbindung

HRID 1876242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876242
C1(C)C=C(C)C=C(C)C=1Cl.[OH:11][C@H:12]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C@H:13]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14]O.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>N1C=CC=CC=1>[OH:11][C@H:12]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C@H:13]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1

Komponenten

5

Edukt 3

HCID 154622-Chloro-1,3,5-trimethylbenzeneHCID 31268PyrrolidineHCID 57331880HCID 57331880, Verbindung

Produkt 1

HCID 59531008HCID 59531008, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Mesityl chloride (0.28 mL, 3.6 mmol) was added slowly to a cold (−10° C.) solution of benzyl (1R,2R)-1,3-dihydroxy-1-(4-methoxyphenyl)propan-2-ylcarbamate (1.07 g, 3.23 mmol) in pyridine (1.5 mL). The mixture was stirred for 30 min and then pyrrolidine (2.7 mL, 33 mmol) was added slowly to the mixture. The mixture was heated to 45° C. for 6 hours and then the solvent was removed to dryness. After purification by column chromatography (SiO2, using a mixture of CH2Cl2, MeOH, NH4OH), the product was obtained as a clear oil (0.816 g, 66% yield).

Aufarbeitung

  1. customthe solvent was removed to dryness
  2. customAfter purification by column chromatography (SiO2
  3. additiona mixture of CH2Cl2, MeOH, NH4OH), the product

Quellen und Nachweise

ORD-Eintrag
ord-3a87849ba318400db85427a524bf993e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309593B2

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