Dimethylamine → Tert-butyl 3-(dimethylamino)azetidine-1-carboxylate

HRID 2066159Notes

Reaction equation

HRID 2066159 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].[CH3:13][NH:14][CH3:15]>CO.O1CCCC1.C(O)(=O)C.[Pd]>[CH3:13][N:14]([CH3:15])[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

7

Reactant 2

HCID 674DimethylamineHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23145930Tert-butyl 3-(dimethylamino)azetidine-1-carboxylateYield 101%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-Boc-azetidin-3-one (3.45 g) in methanol (175 ml) were added a 2M solution of dimethylamine in tetrahydrofuran (21.9 ml), acetic acid (1.73 ml), 10% palladium on carbon (2.15 g), followed by stirring at room temperature under a hydrogen atmosphere for 14 hr. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The combined organic layer was dried over anhydrous sodium sulfate, which was concentrated to provide the titled compound as a colorless oil (4.07 g, 101%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate, which
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-609bffe2df6e4b6484bb6258abc75f4e
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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