1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 3-Amino-1-(diphenylmethyl)azetidine

HRID 366466

Reaction equation

HRID 366466 reaction equation
S(O[CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(C)(=O)=O.C1(=O)[NH:27]C(=O)C2=CC=CC=C12.[K]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[NH2:27][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1

Participants

5

Reactant 2

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 57445463-Amino-1-(diphenylmethyl)azetidine

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

3-Mesyloxy-1-benzhydrylazetidine (30.32 g, 95.5 mmol), potassium phthalimide (21.59 g, 116.53 mmol) and hexadecyl tributylphosphonium bromide (5.92 g, 11.7 mmol) were added to toluene (600 mL) and the mixture stirred at room temperature overnight. The reaction was then heated at reflux for 3 h. The solid was removed by filtration, washed with EtOAc and the combined organics then washed with H2O. After drying over Na2SO4, the organics were treated with charcoal and then concentrated to an oil. Addition of isopropyl ether induced crystallization of the product (16.37 g, 46%).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 3 h
  3. customThe solid was removed by filtration
  4. washwashed with EtOAc
  5. washthe combined organics then washed with H2O
  6. dry with materialAfter drying over Na2SO4
  7. additionthe organics were treated with charcoal
  8. concentrationconcentrated to an oil
  9. additionAddition of isopropyl ether
  10. customcrystallization of the product (16.37 g, 46%)

Sources & evidence

ORD record
ord-7df9b80dab8a4c9aa986b75551577bd6
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Linked notes

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