Methyl iodide → HCID 69528627, compound

HRID 497076Notes

Reaction equation

HRID 497076 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I.[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]1[N:14]([CH3:18])[C:13](=[O:15])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13771167(R)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

Product 1

HCID 69528627HCID 69528627, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF (20 ml) solution of the (5R)-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidin-2-one (5.73 g, 25 mmols) was added dropwise, during cooling with ice, to a THF (100 ml) suspension of NaH (60% oil disp. 1.20 g, 30 mmols), whereafter the mixture was stirred for 30 minutes at room temperature. To the mixture, MeI (7.8 ml, 125 mmols) was added during cooling with ice, and the mixture was stirred for 15 hours at room temperature. During cooling with ice, a saturated aqueous solution (50 ml) of NH4Cl was added, and the solvent was distilled off under reduced pressure. The residue was diluted with water, whereafter the dilution was extracted with AcOEt (50 ml×3), and the organic layer was dried over MgSO4. The solvent was distilled off under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 250 g, MeOH—CHCl3 3:97 v/v) to obtain (5R)-5-[(tert-butyldimethylsilyloxy)methyl]-1-methylpyrrolidin-2-one (6.00 g, 98.8%).

Workup

  1. temperatureduring cooling with ice
  2. stirringthe mixture was stirred for 15 hours at room temperature
  3. temperatureDuring cooling with ice
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe residue was diluted with water, whereafter the dilution
  6. extractionwas extracted with AcOEt (50 ml×3)
  7. dry with materialthe organic layer was dried over MgSO4
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-21051b3c406c470c843c15a3c235f286
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Reaction notes

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