Sodium Bicarbonate → (S)-benzyl 3-(tert-butoxycarbonylamino)-5-ethylidenepiperidine-1-carboxylate

HRID 73534

Reaktionsgleichung

Reaktionsgleichung von HRID 73534
[CH3:1][C:2](C)([O-])C.[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]1[CH2:20][C:19](=O)[CH2:18][N:17]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(=O)(O)[O-].[Na+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[C:7]([O:11][C:12]([NH:14][C@H:15]1[CH2:20][C:19](=[CH:1][CH3:2])[CH2:18][N:17]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 68922849HCID 68922849, Verbindung

Produkt 1

HCID 68922866(S)-benzyl 3-(tert-butoxycarbonylamino)-5-ethylidenepiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of ethyltriphenylphosphonium bromide (11 eq) in 14 mL of THF was added potassium tert-butoxide (10 eq) at room temperature. The reaction mixture was stirred at that temperature for 20 minutes. Then the reaction was cooled to 0° C., and (S)-benzyl 3-(tert-butoxycarbonylamino)-5-oxopiperidine-1-carboxylate (1 eq) in 7 mL of THF was added to the reaction mixture. The reaction was allowed to warm up room temperature. After being stirred for 40 minutes, the reaction mixture was poured into aq. sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated and washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=2:1) to yield (S)-benzyl 3-(tert-butoxycarbonylamino)-5-ethylidenepiperidine-1-carboxylate. LC/MS (m/z): 261.2 (MH+-100), Rt:1.12 min. HPLC: Rt:4.31 min.

Aufarbeitung

  1. temperatureto warm up room temperature
  2. stirringAfter being stirred for 40 minutes
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e6f8476ce6314680b863fca27c4338a2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829193B2

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