Diisopropylethylamine → Tert-butyl 4-[4-(cyclopropylmethylcarbamoyl)-phenyl]-piperidine-1-carboxylate

HRID 1751807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751807
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([OH:3])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=[N:47][C:42]2[CH:43]=[CH:44][CH:45]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C1(CN)CC1>CN(C)C=O>[CH:43]1([CH2:42][NH:47][C:1]([C:4]2[CH:5]=[CH:6][C:7]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][CH2:11]3)=[CH:8][CH:9]=2)=[O:3])[CH2:45][CH2:44]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 66724516Tert-butyl 4-[4-(cyclopropylmethylcarbamoyl)-phenyl]-piperidine-1-carboxylateAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

500 mg tert-butyl 4-(4-carboxyphenyl)-piperidine-1-carboxylate are placed in 28 ml dimethylformamide, then 1.14 ml diisopropylethylamine and 747 mg HATU are added. The reaction mixture is stirred for 15 min at ambient temperature, then 194 mg cyclopropylmethylamine hydrochloride are added. The reaction mixture is stirred overnight at ambient temperature. Then the product is purified by preparative HPLC (method A). 480 mg product are obtained in the form of an oil. Analytical HPLC-MS (method B): RT=1.64 min.

Aufarbeitung

  1. stirringThe reaction mixture is stirred overnight at ambient temperature
  2. customThen the product is purified by preparative HPLC (method A)

Quellen und Nachweise

ORD-Eintrag
ord-09449fd4015740a6b0ec10b78afc4e44
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09161927B2

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