Triethylamine → t-Butyl 4-hydroxy-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate

HRID 1360172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360172
[NH2:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C(N(CC)CC)C.[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.C([O:37]C(=O)CC(C)=O)C>C(Cl)Cl>[OH:8][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH:2]1[NH:1][C:29](=[O:37])[C:28]1[CH:31]=[CH:32][C:25]([C:24]([F:34])([F:33])[F:23])=[CH:26][CH:27]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 123096p-Trifluoromethylbenzyl chlorideHCID 56932104tert-Butyl 3-amino-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 66969609t-Butyl 4-hydroxy-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.50 g (2.3 mmol) of t-butyl 3-amino-4-hydroxypiperidin-1-carboxylate (product of PREPARATION 83) and 0.32 mL, (2.3 mmol) of triethylamine was dissolved in 30 mL of methylene chloride, and 0.34 mL, (2.3 mmol) of 4-trifluoromethyl benzylchloride was dropwise added thereto while stirring at 0° C. for 1 hour, followed by addition of 100 mL of ethylacetoacetate and then washing with water. An organic layer dried over anhydrous magnesium sulfate. The reaction solution was filtered off and distilled off under reduced pressure, then the residue was purified by column chromatography to give 0.48 g (1.2 mmol) of the title compound in a total yield of 54%.

Aufarbeitung

  1. washwashing with water
  2. dry with materialAn organic layer dried over anhydrous magnesium sulfate
  3. filtrationThe reaction solution was filtered off
  4. distillationdistilled off under reduced pressure
  5. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a454667cf7a94e6a9fac05800c786047
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879848B2

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