Reaction #2122480

Reaction equation

1-Methoxy-4-trimethylsilanyloxy-piperidine-4-carbonitrile

HCl

Sodium hydrogen sulfate

→

4-hydroxy-1-methoxy-piperidine-4-carbonitrile

Solvents

water

Conditions

Workup

1. 1
   ExtractionThe aqueous layer was carefully extracted with ethyl acetate three times
2. 2
   Dryingdried over magnesium sulfate
3. 3
   Concentrationconcentrated
4. 4
   OtherThe crude product (ca 94% pure) was used directly for the next step without further purification

Procedure

1-Methoxy-4-trimethylsilanyloxy-piperidine-4-carbonitrile (1.0 g, 4.4 mmol) was slowly added to aqueous HCl (3N) at 15° C. The mixture was stirred for two hours at room temperature and then poured into cold (0° C.) water. Sodium hydrogen sulfate (saturated aqueous solution) was slowly added to adjust the pH to 7. The aqueous layer was carefully extracted with ethyl acetate three times. All organic layers were combined, dried over magnesium sulfate and concentrated. The crude product (ca 94% pure) was used directly for the next step without further purification. Yield: 500 mg of 4-hydroxy-1-methoxy-piperidine-4-carbonitrile (compound P4.2) as light yellow solid.

Source