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

HRID 633916Notes

Reaction equation

HRID 633916 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-5e41e4e614224bc1a40a562c9fc46a44
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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