Réaction #1583869

Équation de réaction

tert-butyl 3-carbonylpyrrolidine-1-carboxylate

MeMgI

water

→

tert-butyl 3-hydroxy-3-methyl-pyrrolidine-1-carboxylate

Solvants

THF

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autrewas conducted at −20° C.
2. 2
   AutreThe resulting reaction solution
3. 3
   Filtrationwas filtered by suction
4. 4
   ExtractionThe filtrate was extracted with dichloromethane
5. 5
   SéchageThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated

Mode opératoire

A solution of tert-butyl 3-carbonylpyrrolidine-1-carboxylate (11.17 g, 0.06 mol) in THF (45 mL) was slowly added to a solution of MeMgI (21.41 g, 0.129 mol) in diethyl ether. The reaction was conducted at −20° C. under stirring for 3 hours. A small amount of water was added to the reaction solution. The resulting reaction solution was filtered by suction. The filtrate was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to produce a crude product of tert-butyl 3-hydroxy-3-methyl-pyrrolidine-1-carboxylate. The above crude product was dissolved in 20 mL 1,4-dioxane. To the resulting solution was introduced an HCl gas. The resulting mixute was stirred overnight and filtered by suction to produce the title product as a red solid (1.67 g) in a yield of 20% (two steps).

Source