Methyl Ethyl Ketone → (R)-1-(4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-benzyl)-3-piperidinecarboxylic acid ethyl ester

HRID 413675

Reaktionsgleichung

Reaktionsgleichung von HRID 413675
[I-].[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20](=O)[CH2:21][CH3:22]>CCOCC.O>[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:19][C:20]2[CH:22]=[CH:21][C:20]([CH:19]3[C:21]4[CH:22]=[CH:5][CH:7]=[CH:8][C:20]=4[CH2:19][CH2:22][C:21]4[CH:10]=[CH:11][CH:12]=[CH:19][C:20]3=4)=[CH:22][CH:21]=2)[CH2:8]1)=[O:6])[CH3:3]

Komponenten

7

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 185582ethyl (3R)-piperidine-3-carboxylate

Produkt 1

HCID 53835769(R)-1-(4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-benzyl)-3-piperidinecarboxylic acid ethyl esterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of the above iodide (1.80 g, 0.0044 mol), (R)-3-piperidinecarboxylic acid ethyl ester (0.69 g, 0.0044 mol) and anhydrous potassium carbonate (1.82 g, 0.0132 mol) in 2-butanone (30 ml) was heated to 50° C. for 6 h. After cooling, the mixture was diluted with ether (50 ml) and water (50 ml) and the phases were separated. The organic phase was washed with water (30 ml) and dried (MgSO4). The solvent was evaporated in vacuo and the oily residue (2.1 g) was purified by gradient column chromatography on silica gel (40 g) using benzene and ethyl acetate as eluents. The benzene/ethyl acetate (9:1) fraction afforded 1.50 g (77%) of (R)-1-(4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-benzyl)-3-piperidinecarboxylic acid ethyl ester.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe phases were separated
  3. washThe organic phase was washed with water (30 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe oily residue (2.1 g) was purified by gradient column chromatography on silica gel (40 g)

Quellen und Nachweise

ORD-Eintrag
ord-58df006fae444ce5a99798597a2d0096
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569849B1

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