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

HRID 492887Notes

Reaction equation

HRID 492887 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([N:11]1[CH2:14][C:13](=O)[CH2:12]1)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>O1CCCC1.C(O)(=O)C.CO.[C].[Pd]>[CH3:1][N:2]([CH3:3])[CH:13]1[CH2:14][N:11]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:12]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 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After adding a 2 M solution of dimethylamine in tetrahydrofuran (21.9 ml), acetic acid (1.73 ml) and 10% palladium-carbon (2.15 g) to a solution of 1-Boc-azetidin-3-one (3.45 g) in methanol (175 ml), the mixture was stirred for 14 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The combined organic layers were dried over anhydrous sodium sulfate. This was followed by concentration to provide the title compound (4.07 g, 101%) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationThis was followed by concentration

Sources & evidence

ORD record
ord-0c7a01e0498043d8909908dea57d59c0
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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