3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-(methylamino)azetidine-1-carboxylate

HRID 492918Notes

Reaction equation

HRID 492918 reaction equation
[C:1]([N:8]1[CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:14][NH2:15]>CO.[C].[Pd]>[CH3:14][NH:15][CH:10]1[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

5

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 6364545Methylamine hydrochloride

Product 1

HCID 23153172tert-Butyl 3-(methylamino)azetidine-1-carboxylateYield 82.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-Boc-azetidin-3-on (240 mg) in methanol (20 ml) were added methylamine hydrochloride (1.42 g) and 10% palladium carbon (1.0 g), followed by stirring under hydrogen atmosphere at room temperature for 60 hours. The reaction mixture was filtered to remove the catalyst. To the filtrate was added again 10% palladium carbon (1.0 g), followed by stirring under hydrogen atmosphere (0.40 MPa) at room temperature for 9 hours. The reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure. To the resultant residue were added a saturated aqueous solution of sodium hydrogencarbonate, ethyl acetate and potassium carbonate, followed by partition. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to provide a crude product of the title compound (216 mg) as a pale yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. additionTo the filtrate was added again 10% palladium carbon (1.0 g)
  4. stirringby stirring under hydrogen atmosphere (0.40 MPa) at room temperature for 9 hours
  5. filtrationThe reaction mixture was filtered
  6. customto remove the catalyst
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionTo the resultant residue were added a saturated aqueous solution of sodium hydrogencarbonate, ethyl acetate and potassium carbonate
  9. customby partition
  10. extractionThe aqueous layer was extracted with ethyl acetate
  11. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6776112c92174123a7f6f89f67e945b5
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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