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

HRID 1437235Notes

Reaction equation

HRID 1437235 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([N:19]1[CH2:22][CH:21]([OH:23])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH3:1][S:2]([O:23][CH:21]1[CH2:22][N:19]([CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:20]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

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

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under cooling with ice, methanesulfonyl chloride (0.68 mL) was added dropwise to 1-benzhydrylazetidin-3-ol (1.50 g) in pyridine (12 mL), followed by stirring at room temperature overnight. Ice-water was added to the reaction mixture, and the precipitated material was recovered by filtration, to thereby give the title compound (890 mg, 45%).

Workup

  1. filtrationthe precipitated material was recovered by filtration

Sources & evidence

ORD record
ord-568b71922fc741d19121e0a1082a49f6
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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