4-Methylmorpholine → Benzyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate

HRID 412234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412234
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([OH:19])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH3:36][NH:37][O:38][CH3:39]>C1COCC1>[CH3:39][O:38][N:37]([CH3:36])[C:17]([CH:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1)=[O:19]

Komponenten

6

Edukt 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

Produkt 1

HCID 22258974Benzyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a cooled (−15° C. to −20° C.) and stirred solution of 1-[(benzyloxy)carbonyl]-3-piperidinecarboxylic acid (4.0 g, 15.2 mmol) in dry THF (50 mL) including methylmorpholine (2 mL) was added dropwise a solution of isobutyl chioroformate (2.28 g, 16.7 mmol) in THF (10 mL). After the mixture was stirred at the same temperature for 20 min, a solution of N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.7 mmol) in THF (20 mL) including methylmorpholine (2 mL) was added. The reaction mixture was allowed to warm to room temperature, and then stirred for 16 hrs. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The separated organic phase was washed with 1N HCl, saturated NaHCO3, and brine, successively. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give benzyl 3-{[methoxy(methyl)amino]carbonyl)-1-piperidinecarboxylate as a colorless oil (4.7 g, yield; quant.).

Aufarbeitung

  1. temperatureTo a cooled (−15° C. to −20° C.)
  2. additionwas added
  3. stirringstirred for 16 hrs
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. custompartitioned between ethyl acetate and water
  6. washThe separated organic phase was washed with 1N HCl, saturated NaHCO3, and brine
  7. dry with materialThe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give

Quellen und Nachweise

ORD-Eintrag
ord-cf62b3c5fc4e4da3ae1d19af887b5680
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562811B1

Notizen zur Reaktion

Wird geladen…