N-Trimethylsilyl-N-methylacetamide → N-(2-hydroxy-1-phenylethyl)-benzamide

HRID 3697

Reaktionsgleichung

Reaktionsgleichung von HRID 3697
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].CN([Si](C)(C)C)C(=O)C.CC([O:23][CH2:24][C:25]1[C:38]2[C:33](=CC=CC=2)[C:32](COC(C)=O)=[C:31]2[C:26]=1C=CC=C2)=O>ClCCl>[OH:4][CH2:3][CH:2]([NH:1][C:24](=[O:23])[C:25]1[CH:38]=[CH:33][CH:32]=[CH:31][CH:26]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 81953N-Trimethylsilyl-N-methylacetamideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 2724025(R)-beta-aminophenethyl alcohol

Produkt 1

HCID 14150746N-(2-hydroxy-1-phenylethyl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A slurry of (R)-2-amino-2-phenylethanol (1.0 g, 7.4 mmol) in 50 mL dichloromethane was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (3.4 mL, 21.1 mmol) until a homogenous solution occured. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobis[benzoyl chloride] (1.0 g, 2.9 mmol) in 20 mL dichloromethane was added. The solution was stirred for 2 hours and 1 mL of 50% aqueous acetic was added causing the crude product to precipitate from solution. This solid was collected by filtration, washed with 1N HCl, water, and recrystallized from dimethylformamide/water to afford 1.2 g of the title compound, mp 235°-236° C.

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C. to 5° C.
  2. customto precipitate from solution
  3. filtrationThis solid was collected by filtration
  4. washwashed with 1N HCl, water
  5. customrecrystallized from dimethylformamide/water

Quellen und Nachweise

ORD-Eintrag
ord-45e1e2f32fac4e2c92640fb69c3a608f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05734081

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