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

HRID 2052344Notes

Reaction equation

HRID 2052344 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.C(N(CC)CC)C.C(O)(=O)/C=C\C(O)=O>C1C=CC=CC=1.C1(C)C=CC=CC=1.C(OCC)C>[CH:6]([N:19]1[CH2:22][CH:21]([O:23][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 444266Maleic Acid

Product 1

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

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Slowly add 1.0 mole of methanesulfonyl chloride to an agitating solution of 1.0 mole 1-benzhydryl-3-hydroxyazetidine and triethylamine in benzene or toluene maintained at 10° to 15° C. Agitate the reaction mixture at 15° to 18° C. for half an hour, then at 20°-23° C. for another half hour. Add diethyl ether and agitate for 10 minutes longer. Remove the triethylamine hydrochloride precipitate by filtration and add the filtrate to a solution of 1.0 mole maleic acid in diethyl ether and stir for about one hour. Isolate the product 1-benzhydryl-3-methanesulfonyloxyazetidine as the hemimaleate salt (1:1) by filtration.

Workup

  1. customRemove the triethylamine hydrochloride precipitate
  2. filtrationby filtration
  3. stirringstir for about one hour

Sources & evidence

ORD record
ord-2ef9414911334dafbb7aa704032cabe1
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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