Reaction #1178457

Reaction equation

sodium hydride

1-tert-butyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

3-bromo-1-propene

→

1-tert-butyl 2-methyl (2R,4R)-4-allyloxypyrrolidine-1,2-dicarboxylate

Yield 96.8%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.WAITthe reaction mixture is left
2. 2
   workup.STIRRINGto stir at room temperature for a further 12 hours
3. 3
   FiltrationThe reaction mixture is then filtered
4. 4
   Otherthe filtrate is evaporated to dryness under reduced pressure
5. 5
   FiltrationAfter the precipitate has been filtered off
6. 6
   Extractionthe filtrate is extracted twice with 20 ml of ethyl acetate each time
7. 7
   DryingDrying of the combined organic phases over sodium sulfate and stripping-off of the solvent

Procedure

1.55 g (38.6 mmol) of sodium hydride are added in portions under nitrogen to the solution of 10.3 g (42 mmol) of 1-tert-butyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate and 36.34 ml (420 mmol) of 3-bromo-1-propene in 100 ml of dimethylformamide (DMF), and the mixture is subsequently stirred at room temperature for 15 minutes. 9.73 g (42 mmol) of silver oxide are then added in portions to the reaction mixture, and the reaction mixture is left to stir at room temperature for a further 12 hours: The reaction mixture is then filtered, the filtrate is evaporated to dryness under reduced pressure, and the residue is taken up in 20 ml of saturated citric acid solution. After the precipitate has been filtered off, the filtrate is extracted twice with 20 ml of ethyl acetate each time. Drying of the combined organic phases over sodium sulfate and stripping-off of the solvent gives 11.6 g of 1-tert-butyl 2-methyl (2R,4R)-4-allyloxypyrrolidine-1,2-dicarboxylate as a red-brown oil; ESI 286.

Source