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

HRID 48472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48472
[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 1.0 L round-bottom flask was charged with K2CO3 (29.2 g; 171 mmol), piperidine (50 g; 163 mmol), and a 1:1 mixture of THF/H2O (800 mL). A 150 mL addition funnel was placed on the flask and charged with CbzCl (29.2 g, 171 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 1 h. The reaction mixture was extracted with EtOAc (500 mL) and the organic layer was washed with water (500 mL), saturated NaCl (500 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material (49.3 g, 100% yield) was carried on without further purification.

Aufarbeitung

  1. additionA 150 mL addition funnel
  2. temperatureThe reaction mixture was warmed to 20° C.
  3. extractionThe reaction mixture was extracted with EtOAc (500 mL)
  4. washthe organic layer was washed with water (500 mL), saturated NaCl (500 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b96d61185a74049914794dfc541726d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703508B2

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