Potassium Carbonate → (R)-N-(3-(tert-butyldimethylsilyloxy)-4-chlorobenzyl)-1-(3-chlorophenyl)ethanamine

HRID 1801602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801602
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:17])=[C:7]([CH:16]=1)[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:26]=[C:27]([C@H:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=1>CN(C=O)C.O.CCOCC>[Si:9]([O:8][C:7]1[CH:16]=[C:3]([CH:4]=[CH:5][C:6]=1[Cl:17])[CH2:2][NH:33][C@@H:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([Cl:24])[CH:26]=1)[CH3:32])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2507697(R)-1-(3-chlorophenyl)ethanamineHCID 59803153(5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane

Produkt 1

HCID 59803157(R)-N-(3-(tert-butyldimethylsilyloxy)-4-chlorobenzyl)-1-(3-chlorophenyl)ethanamineAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (5-(bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane 81 (1.00 g, 2.98 mmol) and potassium carbonate (0.453 g, 3.28 mmol) in DMF was stirred at room temp under N2. (R)-1-(3-Chlorophenyl)ethanamine (0.464 g, 2.98 mmol) was added to the solution and the reaction was stirred at room temperature for 8 h. The reaction was checked by TLC for completion. The reaction mixture was diluted with water and ether. The ether solution was washed with water (2×) and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using a 5% to 30% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give (R)—N-(3-(tert-butyldimethylsilyloxy)-4-chlorobenzyl)-1-(3-chlorophenyl)ethanamine 82 (0.612 g, 50.1% yield) as a colorless oil. The product was carried forth to the next step without further purification.

Aufarbeitung

  1. washThe ether solution was washed with water (2×) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d20668c43fd344b78a780a5811fc7c0e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349831B2

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