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

HRID 1013115Notes

Reaction equation

HRID 1013115 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([CH:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:16]2[CH2:19][CH:18](OS(C)(=O)=O)[CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOCC.C1COCC1.CCOC(C)=O.[Cu]Br>[CH:15]([N:16]1[CH2:19][CH:18]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:17]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 2

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 178418255HCID 178418255, compound

Product 1

HCID 160894471-(Diphenylmethyl)-3-phenylazetidineYield 27%

Reagents, catalysts & solvents 4

HCID 24593copper(I) bromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen mix copper (I) bromide (1.1 g, 7.6 mmol) and anhydrous THF (20 mL). Add a 3.0 M solution of phenylmagnesium bromide in ether slowly (2.5 mL, 7.6 mmol). Stir at RT for 90 min. Dissolve 1-(diphenylmethyl)-3-(methanesulphonyloxy)azetidine (2.0 g, 6.3 mmol) in anhydrous THF (10 mL) and transfer to the reaction mixture. Heat at 50° C. then stir at RT for 16 h. Dilute with EtOAc and wash with saturated aqueous sodium bicarbonate solution. Separate organic layer, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting 10:90 EtOAc:hexanes) to give the title compound (515 mg, 27%).

Workup

  1. temperatureHeat at 50° C.
  2. stirringthen stir at RT for 16 h
  3. washwash with saturated aqueous sodium bicarbonate solution
  4. dry with materialSeparate organic layer, dry (sodium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting 10:90 EtOAc:hexanes)

Sources & evidence

ORD record
ord-2216ef6e3b7941c8b8d80fb3a7feee0d
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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