Реакция #8679

Уравнение реакции

tert-butyl (3S,4S)-3,4-dimethoxy-1-pyrrolidinecarboxylate

tert-Butyl (3S,4S)-3,4-dimethoxy-1-pyrrolidinecarboxylate

→

(3S,4S)-3,4-Dimethoxypyrrolidine

Растворители

hydrochloric acid

Условия реакции

Обработка

1. 1
   ДругоеThe solvent is removed in vacuo
2. 2
   workup.ADDITIONmixed with 1N sodium hydroxide solution
3. 3
   workup.STIRRINGstirred at RT for 10 minutes
4. 4
   ДругоеThe phases are separated
5. 5
   Экстракцияthe aqueous phase is extracted several times with DCM
6. 6
   ЭкстракцияThe combined organic phases are extracted with saturated aqueous sodium chloride solution
7. 7
   Другоеdried
8. 8
   Фильтрацияfiltered
9. 9
   Другоеthe solvent is removed in vacuo
10. 10
    Другое872 mg (63% of theory) of the product are obtained

Методика

2.30 g (9.35 mmol; 94% pure) of tert-butyl (3S,4S)-3,4-dimethoxy-1-pyrrolidinecarboxylate (example XVI, step 2) are taken up in 50 ml of hydrochloric acid (4M in dioxane) and stirred at RT overnight. The solvent is removed in vacuo, and the residue is suspended in DCM, mixed with 1N sodium hydroxide solution and stirred at RT for 10 minutes. The phases are separated and the aqueous phase is extracted several times with DCM. The combined organic phases are extracted with saturated aqueous sodium chloride solution, dried and filtered, and the solvent is removed in vacuo. 872 mg (63% of theory) of the product are obtained.

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