Reaktion #40694

Reaktionsgleichung

t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamate

3-nitrobenzyl bromide

tetrabutylammonium sulfate

sodium hydroxide

→

title compound

Ausbeute 76.6%

t-butyl (1S)-2-(3-methylphenoxy)-1-{[(3-nitrobenzyl)oxy]methyl}ethylcarbamate

Ausbeute 76.6%

Lösungsmittel

benzene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenafter washing with water
2. 2
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
3. 3
   SonstigeThe solvent was evaporated
4. 4
   Sonstigethe obtained crude product
5. 5
   Sonstigewas purified by silica gel chromatography (ethyl acetate-hexane)

Vorschrift

To t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamate (300 mg) obtained in Step 1 of Example 118 were added 3-nitrobenzyl bromide (254 mg), tetrabutylammonium sulfate (91 mg), benzene (2.3 ml) and 50% aqueous sodium hydroxide solution (2.3 ml), and the mixture was stirred at room temperature for 1.5 hrs. The mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give the title compound (340 mg).

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