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

HRID 415264

Reaktionsgleichung

Reaktionsgleichung von HRID 415264
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](Cl)=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=[O:18])[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])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 (0.85 g, 3 mmol) and methyl 3-amino-2-hydroxybenzoate (0.6 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 of 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-faafd834cb3742299273fd569fedd672
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

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