反応 #48626

反応方程式

sodium borohydride

4-(R)-[3-(3-acetoxyphenyl)-1-(R)-hydroxy-2-(S)-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

→

desired compound

4-(R)-[2-(S)-Amino-1-(S)-hydroxy-3-(3-hydroxyphenyl)-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

溶媒

methanol

反応条件

後処理

1. 1
   温度Cool in an ice bath
2. 2
   濃縮And concentrate
3. 3
   その他Partition the residue between ethyl acetate (200 mL) and water (200 mL)
4. 4
   ろ過filter through Celite®
5. 5
   洗浄wash with ethyl acetate
6. 6
   洗浄Wash the organic layer with saturated aqueous sodium chloride
7. 7
   抽出extract with ethyl acetate
8. 8
   乾燥dry (magnesium sulfate)
9. 9
   ろ過filter
10. 10
    濃縮concentrate

実験手順

Add nickel (II) chloride (6.0 g, 46.1 mmol) to a solution of 4-(R)-[3-(3-acetoxyphenyl)-1-(R)-hydroxy-2-(S)-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (18.37 g, 41.9 mmol) in dry methanol (900 mL). Cool in an ice bath and portionwise sodium borohydride (6.34 g, 167.6 mmol) over 8 minutes. Stir for 10 minutes. And concentrate. Partition the residue between ethyl acetate (200 mL) and water (200 mL), filter through Celite® and wash with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride, combine aqueous washes and extract with ethyl acetate. Combine the organic layers, dry (magnesium sulfate), filter and concentrate to give the desired compound as a crude foam. Suspend the Celite® cake in ethyl acetate, filter, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to obtain more desired compound.

出典