Chloromethyl Methyl Ether → HCID 86675837, compound

HRID 1913543Notes

Reaction equation

HRID 1913543 reaction equation
[H-].[Na+].[CH3:3][C@@H:4]1[CH2:9][NH:8][C:7](=[O:10])[CH2:6][O:5]1.[CH3:11][O:12][CH2:13]Cl>O1CCCC1>[CH3:11][O:12][CH2:13][N:8]1[CH2:9][C@@H:4]([CH3:3])[O:5][CH2:6][C:7]1=[O:10]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 54310878(6R)-6-methylmorpholin-3-one

Product 1

HCID 86675837HCID 86675837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To sodium hydride (63%, 4.4 g, 116 mmol) suspended in tetrahydrofuran (100 mL), a solution of (6R)-6-methylmorpholin-3-one (EP350002) (12.1 g) in tetrahydrofuran (50 mL) was added dropwise over 30 minutes under ice cooling. The mixture was stirred at the same temperature for 30 minutes and then further stirred at room temperature for 30 minutes. A solution of chloromethyl methyl ether (10 mL) in tetrahydrofuran (50 mL) was added dropwise thereto over 30 minutes under ice cooling. The mixture was stirred for 30 minutes under ice cooling and then stirred overnight at room temperature. An appropriate amount of water for partition was added thereto, followed by several extractions with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluting solvent: hexane-hexane/ethyl acetate=40/60) to obtain the title compound (7.86 g).

Workup

  1. stirringfurther stirred at room temperature for 30 minutes
  2. waitover 30 minutes under ice cooling
  3. stirringThe mixture was stirred for 30 minutes under ice cooling
  4. stirringstirred overnight at room temperature
  5. customAn appropriate amount of water for partition
  6. additionwas added
  7. extractionfollowed by several extractions with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (eluting solvent: hexane-hexane/ethyl acetate=40/60)

Sources & evidence

ORD record
ord-dca51d4f05bb4ad581387cc9d1247ca4
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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