Реакция #2122480

ord-04a7f95571e44b189f82c934de6ce355

Уравнение реакции

CON1CCC(C#N)(O[Si](C)(C)C)CC1
1-Methoxy-4-trimethylsilanyloxy-piperidine-4-carbonitrile
Cl
HCl
O=S(=O)([O-])O.[Na+]
Sodium hydrogen sulfate
CON1CCC(O)(C#N)CC1
4-hydroxy-1-methoxy-piperidine-4-carbonitrile

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

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

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08574607B2uspto-grants-2013_11