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

HRID 1177178Notes

Reaction equation

HRID 1177178 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]2[CH2:16][CH:15]([OH:17])[CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(CC)CC>C1(C)C=CC=CC=1>[CH:12]([N:13]1[CH2:16][CH:15]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14]1)([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

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

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateYield 41.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methane sulphonyl chloride (0.5 mL, 6.43 mmol) was added to a solution of 1-(diphenylmethyl)-3-hydroxyazetidine (1.38 g, 5.77 mmol) and Et3N (0.9 mL, 6.46 mmol) in toluene (10 mL) at 0° C. The reaction mixture was stirred and warmed to room temperature overnight. The mixture was quenched with H2O (100 mL) and extracted with EtOAc (100 mL). The organic layer was dried over MgSO4 and concentrated to give pale yellow oil (756 mg, 41%) which was used without further purification.

Workup

  1. customThe mixture was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-475203b5ee6f47008cd3233bcf7897f4
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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