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

HRID 2066275Notes

Reaction equation

HRID 2066275 reaction equation
CS(O[CH2:6][CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)(=O)=O.[CH3:18][NH:19][CH3:20]>CO.O1CCCC1>[CH3:18][N:19]([CH2:6][CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)[CH3:20]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Product 1

HCID 23145924Tert-butyl 3-((dimethylamino)methyl)azetidine-1-carboxylateYield 79.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl 3-[(methanesulfonyloxy)methyl]azetidine-1-carboxylate (1.05 g) in methanol (20 ml) was added a 2M solution of dimethylamine in tetrahydrofuran (20 ml), followed by heating in a sealed tube at 70° C. for 40 hr. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was concentrated, and partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed to provide the titled compound as a yellow oil (678 mg, 79.9%).

Workup

  1. temperatureto cool down to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-db027d3b292941ba8a4f481c16212e61
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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