benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate → Benzyl-3-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate

HRID 415306

Reaktionsgleichung

Reaktionsgleichung von HRID 415306
Cl[C:2]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)=[O:3].[NH2:20][C:21]1[C:22]([OH:31])=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25]>ClCCl>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][CH:4]([C:2](=[O:3])[NH:20][C:21]2[CH:30]=[CH:29][CH:28]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:22]=2[OH:31])[CH2:5]1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 2776575benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylateHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Produkt 1

HCID 66621331Benzyl-3-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzyl 3-(chlorocarbonyl)piperidine-1-carboxylate (500 mg, 3 mmol) and methyl 3-amino-2-hydroxybenzoate (1.014 g, 3.6 mmol) were added in anhydrous dichloromethane (20 mL) and the mixture was stirred at room temperature overnight. The mixture was extracted with dichloromethane (100 mL×4) and the organic phase was dried with anhydrous sodium sulfate and evaporated under reduced pressure. 1.2 g benzyl-3-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate was obtained. Yield: 97%. LC-MS (ESI) m/z: 413 (M+1)+.

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane (100 mL×4)
  2. dry with materialthe organic phase was dried with anhydrous sodium sulfate
  3. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3803e9b9c49f4cbc82b19b5be917c2cc
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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