Water → tert-Butyl 3-(methoxymethyl)azetidine-1-carboxylate

HRID 1910397Notes

Reaction equation

HRID 1910397 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1.[H-].[Na+].[CH3:16]I.O>CN(C=O)C>[CH3:16][O:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 66570673tert-Butyl 3-(methoxymethyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (1.0 g) in DMF (20 ml) was added NaH (235 mg; 60% oil suspension) under nitrogen atmosphere, and the mixture was stirred for 30 minutes at room temperature. MeI (665 μl) was added to the mixture, and the whole was stirred for 2 hours. Water was added to the mixture, and the whole was extracted with EtOAc. The extract was washed with water and brine and dried over MgSO4. Concentration under reduced pressure gave a residue, which was purified with silica gel chromatography eluting with n-hexane:EtOAc=5:1 to give tert-butyl 3-(methoxymethyl)azetidine-1-carboxylate (1.04 g).

Workup

  1. stirringthe whole was stirred for 2 hours
  2. extractionthe whole was extracted with EtOAc
  3. washThe extract was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration under reduced pressure
  6. customgave a residue, which
  7. customwas purified with silica gel chromatography
  8. washeluting with n-hexane

Sources & evidence

ORD record
ord-d1e880715b824fbc9a1eaf8278cadc69
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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