Tetrahydrofuran → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

HRID 2172016Notes

Reaction equation

HRID 2172016 reaction equation
[CH2:1]([CH:8]1N[CH:10]([CH2:12][C:13]2[CH:18]=CC=CC=2)[CH:9]1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([N:27]([CH2:30][CH3:31])[CH2:28]C)C.C1C[O:35]CC1>>[CH3:20][S:21]([O:23][CH:31]1[CH2:28][N:27]([CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:9]=[CH:10][CH:12]=[CH:13][CH:18]=2)[CH2:30]1)(=[O:35])=[O:22]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131731899Dibenzylazetidin-3-ol

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateYield 92%

Procedure

To a solution of dibenzylazetidin-3-ol (500 mg, 2.09 mmol) in THF (21 mL) at 0° C. under nitrogen was added methanesulfonyl chloride (194 μL, 2.51 mmol) and triethylamine (612 μL, 4.39 mmol). The reaction mixture was stirred for 1 h then concentrated to dryness. The residue was dissolved in dichloromethane, washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated to dryness to give the title product (0.61 g, 92%) as a yellow oil.

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3616ae58b70f4738b3e465db497c9c1f
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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