Tert-butyl 3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidine-1-carboxylate → N-(4-fluoro-2-methylphenyl)-N-methylazetidin-3-amine

HRID 72426Notes

Reaction equation

HRID 72426 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:20])[CH:9]2[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[C:4]([CH3:21])[CH:3]=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:20])[CH:9]2[CH2:12][NH:11][CH2:10]2)=[C:4]([CH3:21])[CH:3]=1

Participants

3

Reactant 1

HCID 67958638Tert-butyl 3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidine-1-carboxylate

Product 1

HCID 67958130N-(4-fluoro-2-methylphenyl)-N-methylazetidin-3-amineYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of tert-butyl 3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidine-1-carboxylate (D33) 8170 mg, 0.577 mmol) in dichloromethane (1 ml) trifluoroacetic acid/dichloromethane (3/1 ml) was added and the resulting mixture was stirred at room temperature for 1 h. Solvents were evaporated under vacuo and the residue was purified by SPE-SCX cartridge (10 g) eluting with methanol and 2N ammonia in methanol. Ammonia fractions were evaporated in vacuo to afford the title compound (D56) (110 mg)

Workup

  1. customSolvents were evaporated under vacuo
  2. customthe residue was purified by SPE-SCX cartridge (10 g)
  3. washeluting with methanol and 2N ammonia in methanol
  4. customAmmonia fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-cc5c1ba50d1c49e48b140f23ebee2c82
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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