Methanesulfonyl chloride → (1-Benzhydrylazetidin-3-yl)methyl methanesulfonate

HRID 2041972Notes

Reaction equation

HRID 2041972 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1.O>[CH3:20][S:21]([O:13][CH2:12][CH:10]1[CH2:11][N:8]([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2758715(1-Benzhydrylazetidin-3-yl)methanol

Product 1

HCID 21978370(1-Benzhydrylazetidin-3-yl)methyl methanesulfonateYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of [1-(diphenylmethyl)azetidin-3-yl]methanol (30.0 g, 118.4 mmol) in pyridine (200 mL) was slowly added methanesulfonyl chloride (17.0 g, 148.4 mmol), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with water, and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 1N sodium hydroxide, and the ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained solid was washed with hexane to give the title compound (30.3 g, yield 77%) as a pale yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 1N sodium hydroxide
  3. washthe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. washthe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-11d68f53973c4762bbaa2ee88e6f70ac
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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