Water → N-(5-((1R,2S)-2-(3,5-Dimethylbenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 1685900

Reaktionsgleichung

Reaktionsgleichung von HRID 1685900
[NH2:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[CH:22]=O.O>CO>[CH3:18][C:19]1[CH:26]=[C:25]([CH:24]=[C:21]([CH3:22])[CH:20]=1)[CH2:27][NH:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 34225Benzaldehyde, 3,5-dimethyl-HCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

Produkt 1

HCID 44628484N-(5-((1R,2S)-2-(3,5-Dimethylbenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the amine (4) (131 mg, 0.50 mmol) and 3,5-dimethylbenzaldehyde (90 μL, 0.65 mmol) in methanol (5 mL) was added borane-pyridine complex (160 μL, 1.50 mmol) at 40° C. and the resulting mixture was stirred for 1.5 hours. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with a mixed solvent (ethyl acetate:methanol=10:1) and subsequent washing of the organic layer with saturated brine. The organic layer was dried and concentrated and the obtained crude product was purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1) to obtain the desired amine (9) as a white solid (62 mg, Yield: 33%).

Aufarbeitung

  1. extractionfollowed by extraction with a mixed solvent (ethyl acetate:methanol=10:1)
  2. washsubsequent washing of the organic layer with saturated brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe obtained crude product
  6. customwas purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-0329ab4d23a24d03aa862619fca0e448
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148427B2

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