Nipecotic Acid → 1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

HRID 17864

Reaktionsgleichung

Reaktionsgleichung von HRID 17864
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.O1CCCC1>[CH2:12]([O:19][C:20]([N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 4498Nipecotic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×

Produkt 1

HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To an ice cooled solution of nipecotic acid (10.0 g, 77.5 mmol), sodium hydroxide (3.4 g, 85 mmol), and tetrahydrofuran (50 mL) in water (100 mL) was added by simultaneous dropwise addition benzylchloroformate (13.3 mL, 93 mmol) in tetrahydrofuran (50 mL) and sodium hydroxide (3.4 g, 85 mmol) in water (50 mL). Warmed slowly to room temperature. After 24 hours tetrahydrofuran was removed in vacuo and the resulting aqueous mixture acidified with 3 N hydrochloric acid and extracted with dichloromethane (3×). The combined organic portions were dried with anhydrous magnesium sulfate. Filtration followed by evaporation of the filtrate in vacuo gave the titled compound. 1HNMR (CHCl3, 300 MHz) □ 7.45-7.20 (m, 5H); 5.14 (m, 2H); 4.21 (br s, 1H); 3.96 (m, 1H), 3.15 (br s, 1H); 2.93 (m, 1H); 2.51 (m, 1H); 2.09 (m, 1H); 1.80-1.60 (m, 2H); 1.50 (m, 1H) ppm.

Aufarbeitung

  1. customAfter 24 hours tetrahydrofuran was removed in vacuo
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialThe combined organic portions were dried with anhydrous magnesium sulfate
  4. filtrationFiltration
  5. customfollowed by evaporation of the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-41a63700f6cc44a0b5ecf557890effc5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741322B2

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