Reaction #1583869

Reaction equation

tert-butyl 3-carbonylpyrrolidine-1-carboxylate

MeMgI

water

→

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

Solvents

THF

diethyl ether

Conditions

Workup

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

Procedure

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