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

HRID 1712652Notes

Reaction equation

HRID 1712652 reaction equation
[CH3:1][NH:2][CH3:3].CS(O[CH2:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1)(=O)=O>O1CCCC1.CO>[CH3:1][N:2]([CH2:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:11]1)[CH3:3]

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

A 2M solution of dimethylamine in tetrahydrofuran (20 ml) was added to a solution of tert-butyl 3-[(methanesulfonyloxy)methyl]azetidine-1-carboxylate (1.05 g) in methanol (20 ml), and the reaction mixture was heated in a sealed tube at 70° C. for 40 hours. 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 distilled off to give the title compound (678 mg, 79.9%) as a yellow oil.

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. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ffb09161f62641178bc688f651e23906
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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