Methyl iodide → HCID 68671490, compound

HRID 2071114Notes

Reaction equation

HRID 2071114 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:17]I>C1COCC1>[CH3:17][O:3][CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

Product 1

HCID 68671490HCID 68671490, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the sodium hydride (48 mg, 2 mmol) in THF (5 ml) at −78° C., (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate was slowly added. After 15 min, methyl iodide (0.124 ml, 2 mmol) was added and the reaction mixture was slowly allowed to come to rt overnight. Then the reaction mixture was quenched with MeOH and diluted with water (15 ml). Aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried over sodium sulfate and then filtered. The solvent was removed under vacuum, and the crude product was purified by silica gel chromatography (eluting with 15% EtOAc/hexanes) to afford (R)-tert-butyl 2-(methoxymethyl)pyrrolidine-1-carboxylate in 80% yield. (R)-2-(methoxymethyl)pyrrolidine was generated by removal of the Boc protecting group by treatment with trifluoroacetic acid.

Workup

  1. waitto come to rt overnight
  2. customThen the reaction mixture was quenched with MeOH
  3. additiondiluted with water (15 ml)
  4. extractionAqueous layer was extracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed under vacuum
  9. customthe crude product was purified by silica gel chromatography (eluting with 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7197e51203be44f7b002cc39584f4297
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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