Sodium Iodide → HCID 68694074, compound

HRID 644021Notes

Reaction equation

HRID 644021 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:7][O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[CH2:9][O:8][CH3:7]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidine

Product 1

HCID 68694074HCID 68694074, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl bromoacetate (199 μl, 2.10 mmol) was added to a mixture of (S)-2-methoxymethyl pyrrolidine (268 μl, 2.17 mmol), potassium carbonate (319 mg, 2.31 mmol) and sodium iodide (315 mg, 2.10 mmol) in acetonitrile (3 ml). The mixture was subjected to microwave irradiation for 5 min at 160° C., then partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by flash column chromatography eluting with 0-10% (v/v) methanol in dichloromethane afforded (S)-(2-methoxymethyl-pyrrolidin-1-yl) acetic acid methyl ester (133 mg, 0.71 mmol).

Workup

  1. customirradiation for 5 min at 160° C.
  2. custompartitioned between dichloromethane and water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography
  8. washeluting with 0-10% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-3730a3a509e64033adc8c73186ad6296
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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