Citric Acid → tert-Butyl 3-acetylazetidine-1-carboxylate

HRID 64290Notes

Reaction equation

HRID 64290 reaction equation
CON(C)[C:4]([CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5].C[Mg+].[Br-].[C:21](O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:4]([CH:6]1[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:9]1)(=[O:5])[CH3:21]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylateHCID 178418689HCID 178418689, compound

Product 1

HCID 59841137tert-Butyl 3-acetylazetidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate (7.0 g, 28.7 mmol) in THF (150 mL) was added CH3MgBr (43 mL, 43 mmol) at 0° C., then slowly warmed to RT for about 2 hr. 10% aqueous of citric acid (30 mL) was added to the mixture, and extracted with EA (50 mL×3), the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered, concentrated and purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1), to give the crude product (4.0 g, 70%) as a colorless oil. MS (ESI) m/e [M−55]+ 144.0.

Workup

  1. extractionextracted with EA (50 mL×3)
  2. washthe combined organic phases were washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1)

Sources & evidence

ORD record
ord-2987939ee1714866b9a6e359b3c54eed
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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