Methanesulfonyl chloride → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

HRID 2265698Notes

Reaction equation

HRID 2265698 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateYield 44.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-20 °C

Procedure

A suspension of 1-benzhydrylazetidin-3-ol (15.0 g) in pyridine (100 ml) was cooled to −20° C. under a nitrogen atmosphere, and methanesulfonyl chloride (6.33 ml) was added dropwise thereto. The reaction mixture was stirred under a nitrogen atmosphere at −20° C. for 1 hr, then in a water bath for 2.5 days. The reaction mixture was partitioned after addition of water and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. To the residue were added ethanol (10 ml) and hexane (50 ml) to suspend precipitated crystals. The crystals were collected by filtration and washed with hexane. This was dried under aeration at room temperature to provide the titled compound as pale yellow crystals (5.943 g, 44.8%). The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:1, 1:1, then heptane:ethyl acetate:methanol=50:50:1, 40:60:1, then ethyl acetate:methanol=100:1). Fractions containing the target compound were concentrated to provide the titled compound as pale yellow crystals (1.58 g, 11.9%).

Workup

  1. waitin a water bath for 2.5 days
  2. customThe reaction mixture was partitioned
  3. additionafter addition of water and ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. additionTo the residue were added ethanol (10 ml) and hexane (50 ml)
  8. customto suspend precipitated crystals
  9. filtrationThe crystals were collected by filtration
  10. washwashed with hexane
  11. customThis was dried under aeration at room temperature

Sources & evidence

ORD record
ord-2fe4a03f7ffd4223b34b46b0f705dbc4
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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