Hydrochloric Acid → (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

HRID 1517206Notes

Reaction equation

HRID 1517206 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][C@@H:15]1[CH2:19][NH:18][C:17](=[O:20])[CH2:16]1.Cl>CN(C)C=O>[C:9]([Si:6]([CH3:8])([CH3:7])[O:14][C@@H:15]1[CH2:19][NH:18][C:17](=[O:20])[CH2:16]1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1550842-Pyrrolidinone, 4-hydroxy-, (4S)-

Product 1

HCID 11074789(S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-oneYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (93.73 g, 1.26 mol) and tert-butyldimethylsilyl chloride (145.3 g, 0.96 mol) were added to a solution of (S)-4-hydroxy-2-pyrrolidone (92.8 g, 0.92 mol) in dimethylformamide (560 mL). The mixture was then stirred at room temperature for 16 hours, after which time it was poured over ice and an aqueous solution of hydrochloric acid (0.2 M, 300 mL) was added. The mixture was stirred at room temperature for 10 minutes, and then extracted with ethyl acetate (4×500 mL). The combined organic extracts were washed with brine (1000 mL), dried over sodium sulphate, filtered, and evaporated under reduced pressure to give (S)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one as a solid (200 g, 100%).

Workup

  1. additionafter which time it was poured over ice
  2. stirringThe mixture was stirred at room temperature for 10 minutes
  3. extractionextracted with ethyl acetate (4×500 mL)
  4. washThe combined organic extracts were washed with brine (1000 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4c427f98e4d84461943f225f02e56048
Source dataset
uspto-grants-2012_07
Patent number
US08232269B2

Reaction notes

Loading…