1,2-Dichloroethane → 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester

HRID 559312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559312
[CH3:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[CH2:29]([O:31][C:32]([CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])[CH3:30]>C(Cl)Cl>[CH2:29]([O:31][C:32]([CH:34]1[CH2:39][CH2:38][N:37]([C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:7])[CH2:36][CH2:35]1)=[O:33])[CH3:30]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 757711-HydroxybenzotriazoleHCID 813261-Methylcyclopropanecarboxylic acid

Produkt 1

HCID 594381441-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-methyl-cyclopropanecarboxylic acid (14.4 g, 0.144 mol) in 200 mL of CH2Cl2 was added (27.10 g, 0.141 mol) of EDC, (19.10 g, 0.141 g) of HOBt and Et3N (35.93 mL, 0.259 mol). After one hour at RT, was added piperidine-4-carboxylic acid ethyl ester (18.90 g, 0.120 mol). The mixture was stirred at RT over night and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated under vacuo. Column chromatography (SiO2, EtOAc/H, 1:1) yielded 26.1 g (92%) of the title compound as a light yellow oil.

Aufarbeitung

  1. additionpoured onto water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7dabbae6d6764d53ac6a46c45b0a44f9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063075B2

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