Réaction #8679

Équation de réaction

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

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

→

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

Solvants

hydrochloric acid

Conditions de réaction

Traitement

1. 1
   AutreThe 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
   AutreThe phases are separated
5. 5
   Extractionthe aqueous phase is extracted several times with DCM
6. 6
   ExtractionThe combined organic phases are extracted with saturated aqueous sodium chloride solution
7. 7
   Autredried
8. 8
   Filtrationfiltered
9. 9
   Autrethe solvent is removed in vacuo
10. 10
    Autre872 mg (63% of theory) of the product are obtained

Mode opératoire

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.

Source