Sodium hydride → HCID 57419607, compound

HRID 253550Notes

Reaction equation

HRID 253550 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[CH3:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26]I.[H-].[Na+]>C1COCC1.CCOCC>[CH3:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:1][CH:2]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH2:4]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 227078941-Iodo-4-methoxybutaneHCID 46831646HCID 46831646, compound

Product 1

HCID 57419607HCID 57419607, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 3-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylate (205 mg, 0.74 mmol) and 4-methoxybutyl iodide (750 mg, 3.5 mmol) in dry THF (5 mL) under N2 was added 60& NaH in oil (0.14 g, 3.5 mmol). H2 evolution occurred. The mixture was heated at reflux for 8 h. The mixture was cooled, diluted with ether (90 mL), and washed with water (25 mL) and brine (25 mL), and dried over MgSO4. Removal of the solvent left an oil which was purified by flash chromatography on a 12-g silica cartridge eluted with a 0 to 100% EtOAc in hexanes gradient to afford tert-butyl 3-((4-methoxybutoxy)(phenyl)methyl)pyrrolidine-1-carboxylate (47 mg, 17%) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 8 h
  3. temperatureThe mixture was cooled
  4. washwashed with water (25 mL) and brine (25 mL)
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent
  7. waitleft an oil which
  8. customwas purified by flash chromatography on a 12-g silica cartridge
  9. washeluted with a 0 to 100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-ead2a60a37434afb941e933482115361
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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