Triethylamine → cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

HRID 931302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931302
C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.CC1CCNCC1C(OCC)=O.C(N(CC)CC)C.[CH3:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]>ClCCl>[CH3:35][C@H:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:46])[CH3:47])=[O:43])[CH2:38][C@H:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 13658603Ethyl 4-methylpiperidine-3-carboxylateHCID 707916011-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

Produkt 1

HCID 131735164cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Di-tert-butyl dicarbonate (3.26 g, 15.20 mmol) was added to a solution of ethyl 4-methylpiperidine-3-carboxylate (2.0 g, 11.68 mmol) and triethylamine (3.9 mL, 28.05 mmol) in anhydrous dichloromethane (50 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The mixture partitioned between dichloromethane and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a mixture of the cis and trans diastereomers of 1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (3.0 g). The crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether) to afford cis-1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (2.5 g).

Aufarbeitung

  1. customThe mixture partitioned between dichloromethane and water
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford
  6. customThe crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-4a634299e5f74e8d8bc683344d04df11
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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