4-Methylmorpholine → 2-(2-Oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1823932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823932
[C:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[NH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].O[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=N1.CN(C)CCCCN=C=NCC.CN1CCOCC1>ClCCl.O>[C:25]1([C:23]2[N:34]=[C:35]([CH:40]3[CH2:39][CH2:38][CH2:37][CH2:36][NH:32]3)[NH:21][CH:22]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:4]([O:3][C:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:19])[NH:21][CH2:22][C:23](=[O:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

9

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 688345(S)-1-N-Cbz-Pipecolinic acidHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 21914090(4-Dimethylamino-butyl)-ethyl-carbodiimide

Produkt 2

HCID 235707182-(2-Oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl esterHCID 178420113HCID 178420113, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-1-(Carbobenzyloxy)-2-piperidinecarboxylic acid (15.8 g, 60 mmol), 2-amino-1phenyl-ethanone hydrochloride (10.30 g, 60 mmol), and HOBT (1-hydroxybenzo-triazole) (16.20 g, 120 mmol) were mixed in dichloromethane (400 mL). The stirring mixture was cooled to 0° C. and then (4-dimethylamino-butyl)-ethyl-carbodiimide (14.90 g, 78 mmol) and NMM (N-methyl-morpholine) (7.27 g, 72 mmol) were added. The reaction mixture was then warmed to room temperature. After 16 hours the reaction mixture was treated with water, and the resulting solid was filtered. The organic phase from the filtrate was separated and washed consecutively with saturated NaHCO3, 2N citric acid, and saturated NaHCO3 once again, then dried over MgSO4, filtered, and concentrated to yield the title product 2-(2-oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester as a yellow oil, which was used without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was then warmed to room temperature
  2. filtrationthe resulting solid was filtered
  3. customThe organic phase from the filtrate was separated
  4. washwashed consecutively with saturated NaHCO3, 2N citric acid, and saturated NaHCO3 once again
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-adeb1121502a4c3eba558bee447a4e46
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041681B2

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