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

HRID 1712644Notes

Reaction equation

HRID 1712644 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 down to −20° C. under a nitrogen atmosphere, and methanesulfonyl chloride (6.33 ml) was added dropwise. The reaction mixture was stirred under a nitrogen atmosphere at −20° C. for 1 hour, 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. Ethanol (10 ml) and hexane (50 ml) was added to the residue, and the precipitated crystals were suspended. The crystals were collected by filtration and washed with hexane. This was dried under aeration at room temperature to give the title compound (5.943 g, 44.8%) as pale yellow crystals. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:1, 1:1, heptane:ethyl acetate:methanol=50:50:1. 40:60:1, then ethyl acetate:methanol=100:1). The fractions containing the target compound were concentrated to give the title compound (1.58 g, 11.9%) as pale yellow crystals.

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. additionEthanol (10 ml) and hexane (50 ml) was added to the residue
  8. filtrationThe crystals were collected by filtration
  9. washwashed with hexane
  10. customThis was dried under aeration at room temperature

Sources & evidence

ORD record
ord-dbe3ec8160864ef3963dcd812aeb9879
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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