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

HRID 2085452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085452
[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][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

7

Edukt 4

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

Produkt 1

HCID 11481889((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of the (2R)-2-phenylpropylamine (1.2g, 8.87mmol) in hexane (16.0 mL) was added triethylamine (2.47 mL, 17.74 mmol) and 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 IN 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=6.9Hz), 1.29(d, 3H, J=6.9Hz), 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 IN 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-1295869916a84999809be9b534370de8
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720357B2

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