Benzyl Bromide → (S)-N-Benzyl-1(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

HRID 1541

Reaktionsgleichung

Reaktionsgleichung von HRID 1541
[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][C@@H:15]([OH:27])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:30]([N:17]([CH2:16][C@H:15]([OH:27])[CH2:14][O:13][C:12]1[CH:28]=[CH:29][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 9908577(S)-1-(4-Benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

Produkt 1

HCID 22883068(S)-N-Benzyl-1(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol (1.9 g, 4.8 mMol) and benzyl bromide (0.57 ml, 4.8 mMol) in dimethylformamide (10 ml) containing sodium carbonate (770 mg, 7.2 mMol) was stirred at room temperature for 18 hours. The mixture was filtered and the residue was washed with ethyl acetate. The filtrates were combined, washed with water and brine, dried and evaporated. Purification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the title compound.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe residue was washed with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customevaporated
  6. customPurification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c88884b2244548bda021d31a20f133fd
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726165

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