Piperidine → (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate

HRID 1160351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160351
[C:1]([O-:4])([O-:3])=O.[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].[CH2:24]1COC[CH2:25]1.O>>[CH2:24]([O:3][C:1]([C@H:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=[O:4])[CH3:25]

Komponenten

5

Edukt 4

HCID 8082PiperidineHCID 10387Benzyl chloroformate2×HCID 11430Potassium CarbonateHCID 21881883Oxolane--water (1/1)

Produkt 1

HCID 40634406(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylateAusbeute 100 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 250 mL round-bottom flask was charged with K2CO3 (13.5 g, 97.6 mmol), piperidine (10 g, 32.5 mmol), and a 1:1 mixture of THF/H2O (100 mL). A 50 mL addition funnel was placed on the flask and charged with CbzCl (6.67 g, 39.0 mmol). The flask was cooled to 0° C. and then CbzCl was added dropwise over 5 minutes. The reaction mixture was warmed to 20° C. and stirred for 12 h. The reaction mixture was extracted with EtOAc (250 mL) and the organic layer was washed with saturated NaCl (250 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material (9.5 g, 100% yield) was carried on without further purification.

Aufarbeitung

  1. additionA 50 mL addition funnel
  2. temperatureThe reaction mixture was warmed to 20° C.
  3. extractionThe reaction mixture was extracted with EtOAc (250 mL)
  4. washthe organic layer was washed with saturated NaCl (250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7e88db9ef1b24e00a125a4e817ad9504
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816375B2

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