Triethylamine → ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine

HRID 392936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392936
[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:27]([S:30](Cl)(=[O:32])=[O:31])([CH3:29])[CH3:28]>CCCCCC.C(Cl)Cl>[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH:9][S:30]([CH:27]([CH3:29])[CH3:28])(=[O:32])=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 824082-Propanesulfonyl chlorideHCID 1547949(R)-(+)-beta-Methylphenethylamine

Produkt 2

HCID 1547949(R)-(+)-beta-MethylphenethylamineHCID 11481889((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amineAusbeute 180,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of the (2R)-2-phenylpropylamine (1.2 g, 8.87 mmol) in hexane (16.0 mL) was added triethylamine (2.47 mL, 17.74 mmol) and is dimethylaminopyridine (0.30 g, 2.47 mmol). Cooled reaction to 5° C., then added a solution of isopropylsulfonyl chloride (0.97 mL, 8.69 mmol) dissolved in methylene chloride (6.0 mL) over a period of 15.0 minutes. Stirred for 45.0 minutes, then stirred at room temperature for 120.0 minutes. Quenched reaction with 1N HCl (20.0 mL) and extracted organic with methylene chloride (25.0 mL). Dried organic layer with anhydrous magnesium sulfate, filtered and concentrated filtrate to provide the final title compound, ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine, (1.93 g, 90.1%) an oil; 1H nmr (CDCl3, 300 MHz) δ 1.25 (d, 3H, J=6.9 Hz), 1.29(d, 3H, J=6.9 Hz), 1.30 (d, 3H, J=7.2 Hz), 2.98 (m, 1H), 3.05 (m, 1H), 3.22 (m, 1H), 3.36 (m, 1H), 3.89 (b, 1H), 7.23 (m, 2H), 7.34 (m, 2H).

Aufarbeitung

  1. temperatureCooled
  2. customreaction to 5° C.
  3. stirringstirred at room temperature for 120.0 minutes
  4. customQuenched
  5. customreaction with 1N HCl (20.0 mL)
  6. extractionextracted organic with methylene chloride (25.0 mL)
  7. filtrationDried organic layer with anhydrous magnesium sulfate, filtered

Quellen und Nachweise

ORD-Eintrag
ord-61351087ad0e4e7c8bb28e84a7f0334f
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803484B2

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