Methyl iodide → tert-Butyl 3-methoxyazetidine-1-carboxylate

HRID 899255Notes

Reaction equation

HRID 899255 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[H-].[Na+].I[CH3:16]>O1CCCC1>[CH3:16][O:1][CH:2]1[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 22243050tert-Butyl 3-methoxyazetidine-1-carboxylateYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (J. Med. Chem. 2001, 44, 94., 130 mg, 0.75 mmol) in tetrahydrofuran (1.5 mL) was added sodium hydride (60% in mineral oil dispersion, 36 mg, 0.90 mmol) slowly at 0° C. After 30 min., iodomethane (130 mg, 0.90 mmol) was added to the mixture at 0° C. The mixture was gradually warmed to room temperature and stirred overnight. The mixture was concentrated and purified by column chromatography on silica gel eluting with hexane/ethyl acetate (6/1) to afford 110 mg (76%) of the title compound as a colorless oil:

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography on silica gel eluting with hexane/ethyl acetate (6/1)

Sources & evidence

ORD record
ord-bbb6bbfe3b1f4f4991931cce997efc2b
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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