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

HRID 2265583Notes

Reaction equation

HRID 2265583 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-fe9ddbacf4774d4a9459e466538357d5
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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