Reaction #8679

Reaction equation

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

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

→

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

Solvents

hydrochloric acid

Conditions

Workup

1. 1
   OtherThe 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
   OtherThe 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
   Otherdried
8. 8
   Filtrationfiltered
9. 9
   Otherthe solvent is removed in vacuo
10. 10
    Other872 mg (63% of theory) of the product are obtained

Procedure

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