Methyl iodide → Methyl (2S)-1-methyl-5-oxoprolinate

HRID 554078Notes

Reaction equation

HRID 554078 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5]1.[H-].[Na+].[CH3:13]I>O1CCCC1>[CH3:13][N:5]1[C:6](=[O:9])[CH2:7][CH2:8][C@H:4]1[C:3]([O:2][CH3:1])=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 78646Methyl 5-oxo-L-prolinate

Product 1

HCID 12361160Methyl (2S)-1-methyl-5-oxoprolinateYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(L)-pyroglutamic acid methyl ester (1 g, 6.99 mmol) was dissolved/mixed with tetrahydrofuran (10 ml) and cooled to 0° C. using an ice-bath. Sodium hydride (0.201 g of a 60% suspension in oil, 8.38 mmol) was added to the mixture. After bubbling stopped, methyl iodide (0.522 ml, 8.38 mmol) was added and the mixture was allowed to warm to room temperature and then stirred for 1 hr. The solvent was evaporated and water was added (1 ml). The aqueous layer was then extracted with dichloromethane. Evaporation of the dichloromethane gave crude methyl 1-methyl-5-oxo-prolinate (0.308 g) which was used in the next step without further purification.

Workup

  1. customAfter bubbling
  2. temperatureto warm to room temperature
  3. customThe solvent was evaporated
  4. additionwater was added (1 ml)
  5. extractionThe aqueous layer was then extracted with dichloromethane
  6. customEvaporation of the dichloromethane

Sources & evidence

ORD record
ord-5eff60058e9b4630808207f89647722d
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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