Réaction #1689268

Équation de réaction

methanol

trimethylchlorosilane

lithium borohydride

(R)-phenylglycine

→

(R)-2-Amino-2-phenylethanol

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture is stirred at room temperature overnight
2. 2
   workup.STIRRINGthe mixture is stirred at room temperature for 2 hours
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue is dissolved
5. 5
   workup.STIRRINGwhile stirring, in 690 ml of a 20% aqueous solution of potassium hydroxide
6. 6
   ExtractionThe aqueous phase is extracted three times with ethyl acetate
7. 7
   LavageThe combined organic phases are washed with water
8. 8
   Séchagedried over magnesium sulphate
9. 9
   Concentrationconcentrated in vacuo

Mode opératoire

20 g (920 mmol) of lithium borohydride are dissolved in 420 ml of absolute tetrahydrofuran. 233.5 ml (1.84 mol) of trimethylchlorosilane are added dropwise, while stirring, and 69.5 g (0.46 mol) of (R)-phenylglycine are then added in portions within the space of 4 hours. The reaction mixture is stirred at room temperature overnight. 690 ml of methanol are then added and the mixture is stirred at room temperature for 2 hours and concentrated in vacuo. The residue is dissolved, while stirring, in 690 ml of a 20% aqueous solution of potassium hydroxide. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulphate and concentrated in vacuo.

Source