反応 #40694

反応方程式

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

3-nitrobenzyl bromide

tetrabutylammonium sulfate

sodium hydroxide

→

title compound

収率 76.6%

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

収率 76.6%

溶媒

benzene

ethyl acetate

反応条件

後処理

1. 1
   洗浄after washing with water
2. 2
   乾燥the organic layer was dried over anhydrous sodium sulfate
3. 3
   その他The solvent was evaporated
4. 4
   その他the obtained crude product
5. 5
   その他was purified by silica gel chromatography (ethyl acetate-hexane)

実験手順

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).

出典