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

HRID 2235038Notes

Reaction equation

HRID 2235038 reaction equation
C(N(CC)CC)C.[C:8]1([CH:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:15]2[CH2:18][CH:17]([OH:19])[CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[C:20]1([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:15]2[CH2:18][CH:17]([O:19][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:16]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (153 mL) was added to a methylene chloride solution (1 L) of 1-diphenylmethyl-3-hydroxyazetidine (239 g) at room temperature, and methanesulfonyl chloride (85 mL) was added dropwise to the mixture under cooling with ice. The mixture was returned to room temperature, and stirred for two hours. The reaction mixture was washed with water (1 L), and the organic layer was dried with sodium sulfate anhydrate, followed by removal of solvent under reduced pressure. The precipitated solid was dispersed in hexane and collected through filtration, to thereby yield 313 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customwas returned to room temperature
  3. washThe reaction mixture was washed with water (1 L)
  4. dry with materialthe organic layer was dried with sodium sulfate anhydrate
  5. customfollowed by removal of solvent under reduced pressure
  6. additionThe precipitated solid was dispersed in hexane
  7. filtrationcollected through filtration

Sources & evidence

ORD record
ord-7c2e24d9958149d8ac2ac2f290d19f62
Source dataset
uspto-grants-2010_05
Patent number
US07713997B2

Reaction notes

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